Tag: 100-200

Synthesis of (5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)methanamine was written by Bai, Zhong-Gang;Qi, Hui;Zhang, Qun-Zheng;Ma, Yu;Pan, Qing;Zhang, Xun-Li. And the article was included in Heterocycles in 2017.Recommanded Product: 1260672-10-3 The following contents are mentioned in the article:

This short paper reports the development of a new method for the synthesis of (5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)methanamine. Pyrazole was initially N-protected with the 2-(trimethylsilyl)ethoxymethyl (SEM) group, followed by alkylation at C-5 position with 1-bromo-3-chloropropane. Following SEM deprotection, the intramol. ring was closed and then a bromine atom (Br) was introduced with N-bromosuccinimide (NBS) by electrophilic aromatic substitution (S_EAr), forming 3-bromo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole. The Br group was subsequently converted into aldehyde group, then into oxime. The final step of hydrogenation resulted in the desired product. The overall yield through the 8-step reaction process was found to be 29.4%. This development provides a novel synthetic route to the formation of 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole skeleton. This study involved multiple reactions and reactants, such as (5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)methanamine (cas: 1260672-10-3Recommanded Product: 1260672-10-3).

(5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)methanamine (cas: 1260672-10-3) belongs to pyrazole derivatives. Pyrazole has two ring nitrogen atoms in which N1 is pyrrolic and N2 is pyridine-like. The N1 nitrogen is not reactive but is deprotonated in the presence of a base-forming anion. Pyrazoles are commonly used scaffold molecules in drug discovery projects. The use of pyrazole derivatives is based on their analgesic, anti-inflammatory, antipyretic, antiarrhythmic, sedative, muscle relaxant, neuroleptic, anticonvulsant, monoamine oxidase inhibitory, antidiabetic and antibacterial activities.Recommanded Product: 1260672-10-3

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

New xanthine oxidase inhibitors of the pyrazolo[3,4-d]pyrimidine and pyrazolo[3,4-b]pyridine class. II. Comparative evaluation of their effectiveness was written by Vartanyan, L. S.;Rashba, Yu. E.;Kazachenko, A. I.;Korbukh, I. A.;Bulychev, Yu. N.;Preobrazhenskaya, M. N.. And the article was included in Khimiko-Farmatsevticheskii Zhurnal in 1982.Reference of 49834-67-5 The following contents are mentioned in the article:

Thirty pyrazolo[3,4-d]pyrimidines I (R = H, CH₂NMe₂, N-methylpiperazinylmethyl, or piperidinylmethyl; R¹ = H, CH₂NEt₂, or N-methylpiperazinylmethyl; R² = H or Me) and II [R = H, CN, CH₂CN, C(NH₂):NOH, etc.; R¹ = SH, SMe, NHNH₂, etc.; R² = H, SH, or SMe] and 5 pyrazolo[3,4-b]pyridines III (R = H or OH; R¹ = H, OH, SH, Cl, or SMe) were tested for xanthine oxidase  [9002-17-9]-inhibiting activity. The kinetics of xanthine oxidase inhibition by I, II, and III was studied. Structure-activity relations are discussed. This study involved multiple reactions and reactants, such as 1H-Pyrazolo[3,4-b]pyridin-4-ol (cas: 49834-67-5Reference of 49834-67-5).

1H-Pyrazolo[3,4-b]pyridin-4-ol (cas: 49834-67-5) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. Protonation of pyrazole in strong acid leads to pyrazolium cations, which undergo electrophilic substitution preferentially at C3 rather than C4. The pyrazole anion is not reactive toward nucleophiles but is mostly reactive to electrophiles.Reference of 49834-67-5

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Nitroolefins. I. A new and convenient access to indolizines and pyrazolo[1,5-a]pyridines using 1-nitro-2-(phenylthio)ethylene was written by Tominaga, Yoshinori;Ichihara, Yuichi;Hosomi, Akira. And the article was included in Heterocycles in 1988.HPLC of Formula: 104468-72-6 The following contents are mentioned in the article:

1-Nitro-2-(phenylthio)ethylene reacts with a variety of N-ylides and N-imines (pyridinium, isoquinolinium, quinolinium, phthalazinium N-ylides and N-imines) in the presence of Et₃N to give the corresponding fused pyrrole and pyrazole derivatives [indolizines I (R = H, R¹ = CO₂Et, CN, R² = H, Me), pyrrolo[2,1-a]isoquinoline, pyrrolo[2,1-a]phthalazine (II, R = H), pyrazolo[1,5-a]pyridine, pyrazolo[5,1-a]quinoline, and pyrazolo[5,1-a]isoquinoline], along with the corresponding 1-nitropyrrolopyridines and 1-nitropyrazolopyridines, e.g., I and II (R = NO₂), resp., in moderate yields. This study involved multiple reactions and reactants, such as 5-Methylpyrazolo[1,5-a]pyridine (cas: 104468-72-6HPLC of Formula: 104468-72-6).

5-Methylpyrazolo[1,5-a]pyridine (cas: 104468-72-6) belongs to pyrazole derivatives. Pyrazole is a weak base, with pKb 11.5 (pKa of the conjugated acid 2.49 at 25 °C).Pyrazole used as a ligand to prepare organometallic compounds. The presence of both electronegative nitrogen atoms in the pyrazole ring reduces the electron density of the C3- and C5-positions leaving electron density of C4-position unaltered. Thus the C4-position is vulnerable to electrophilic attack. The C3 electrophilic-position may undergo deprotonation in the presence of a strong base leading to ring opening.HPLC of Formula: 104468-72-6

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Komatsuda, Masaaki; Suto, Ayane; Kondo, Hiroki Jr; Takada, Hiroyuki; Kato, Kenta; Saito, Bunnai; Yamaguchi, Junichiro published an article in 2022, the title of the article was Ring-opening fluorination of bicyclic azaarenes.HPLC of Formula: 143803-93-4 And the article contains the following content:

Authors have discovered a ring-opening fluorination of bicyclic azaarenes. Upon treatment of bicyclic azaarenes such as pyrazolo[1,5-a]pyridines with electrophilic fluorinating agents, fluorination of the aromatic ring is followed by a ring-opening reaction. Although this overall transformation can be classified as an electrophilic fluorination of an aromatic ring, it is a novel type of fluorination that results in construction of tertiary carbon-fluorine bonds. The present protocol can be applied to a range of bicyclic azaarenes, tolerating azines and a variety of functional groups. Addnl., mechanistic studies and enantioselective fluorination have been examined The experimental process involved the reaction of 4-Methylpyrazolo[1,5-a]pyridine-3-carboxylic acid(cas: 143803-93-4).HPLC of Formula: 143803-93-4

The Article related to pyrazolopyridine bicyclic azaarene ring opening fluorination, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.HPLC of Formula: 143803-93-4

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

On April 21, 2011, Bretschneider, Thomas; Fuesslein, Martin; Koehler, Adeline; Muehlthau, Friedrich August; Franken, Eva-Maria; Voerst, Arnd published a patent.Computed Properties of 1014631-89-0 The title of the patent was Synthesis of 1-(pyrid-3-yl)-pyrazoles and 1-(pyramid-5-yl)-pyrazoles and use as insecticide and/or acaricide.. And the patent contained the following:

The invention relates to the use of partially known heterocyclic compounds for combating animal pests, including arthropods and in particular insects, and further relates to novel heterocyclic compounds and to methods for synthesis thereof. Also disclosed are the rates of effectiveness of selected compounds, relating to the invention, in killing particular insect and acarid pests on sample crops. The experimental process involved the reaction of 1-(Pyridin-3-yl)-1H-pyrazole-4-carboxylic acid(cas: 1014631-89-0).Computed Properties of 1014631-89-0

The Article related to pyridyl pyramidyl pyrazole insecticide acaricide crop protection, Agrochemical Bioregulators: Invertebrate and other aspects.Computed Properties of 1014631-89-0

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

On May 14, 2015, Hatcher, John M.; Zhang, Jinwei; Choi, Hwan Geun; Ito, Genta; Alessi, Dario R.; Gray, Nathanael S. published an article.Synthetic Route of 98138-75-1 The title of the article was Discovery of a Pyrrolopyrimidine (JH-II-127), a Highly Potent, Selective, and Brain Penetrant LRRK2 Inhibitor. And the article contained the following:

Activating mutations in leucine-rich repeat kinase 2 (LRRK2) are present in a subset of Parkinson’s disease (PD) patients and may represent an attractive therapeutic target. Here the authors report JH-II-127 I, as a potent and selective inhibitor of both wild-type and G2019S mutant LRRK2. Compound I substantially inhibits Ser910 and Ser935 phosphorylation of both wild-type LRRK2 and G2019S mutant at a concentration of 0.1-0.3 μM in a variety of cell types and is capable of inhibiting Ser935 phosphorylation in mouse brain following oral delivery of doses as low as 30 mg/kg. The experimental process involved the reaction of 6-Chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine(cas: 98138-75-1).Synthetic Route of 98138-75-1

The Article related to pyrrolopyrimidine brain penetrant lrrk inhibitor, lrrk2, parkinson’s disease, leucine-rich repeat kinase 2, pharmacokinetics, Pharmacology: Structure-Activity and other aspects.Synthetic Route of 98138-75-1

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

On April 10, 2008, Elzein, Elfatih; Kalla, Rao V.; Li, Xiaofen; Perry, Thao; Gimbel, Art; Zeng, Dewan; Lustig, David; Leung, Kwan; Zablocki, Jeff published an article.COA of Formula: C9H7N3O2 The title of the article was Discovery of a Novel A2B Adenosine Receptor Antagonist as a Clinical Candidate for Chronic Inflammatory Airway Diseases. And the article contained the following:

Recently, the authors have reported a series of new 1,3-sym. (R1 = R3) substituted xanthines which have high affinity and selectivity for the human adenosine A2B receptors (hA2B-AdoR). Unfortunately, this class of compounds had poor pharmacokinetic properties. This prompted us to investigate the effect of differential alkyl substitution at the N-1 and N-3 positions (N1-R ≠ N3-R) on A2B-AdoR affinity and selectivity; the authors had the dual objectives of enhancing affinity and selectivity for the A2B-AdoR, as well as improving oral bioavailability. This effort has led to the discovery of compound (I), that displayed high affinity and selectivity for the hA2B-AdoR (Ki = 22 nM). In addition, compound I showed high functional potency in inhibiting the accumulation of cAMP induced by 5′-N-ethylcarboxamidoadenosine in HEK-A2B-AdoR and NIH3T3 cells with KB values of 6 and 2 nM, resp. In a single ascending-dose phase I clin. study, compound I had no serious adverse events and was well tolerated. The experimental process involved the reaction of 1-(Pyridin-3-yl)-1H-pyrazole-4-carboxylic acid(cas: 1014631-89-0).COA of Formula: C9H7N3O2

The Article related to adenosine receptor antagonist preparation antiinflammatory inflammatory airway disease pharmacokinetics, Pharmacology: Structure-Activity and other aspects.COA of Formula: C9H7N3O2

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Robins, Roland K. published an article in 1957, the title of the article was Potential purine antagonists. IX. Further studies of some 4,6-disubstituted-pyrazolo[3,4-d]pyrimidines.Application In Synthesis of 6-Chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine And the article contains the following content:

[The 4,6-disubstituted-pyrazolo[3,4-d]pyrimidines are represented in this abstract by Z, followed in parentheses by the 4- and the 6-substituent, resp.] Powd. Z(HO,HO) (I) (200 g.), 1300 cc. POCl3, and 500 cc. PhNEt2 refluxed 2 hrs., about 900 cc. excess POCl3 removed in vacuo on the steam bath, the sirupy residue poured with stirring onto crushed ice and H2O and extracted with Et2O, the extract evaporated, the residue (128 g.) extracted 5 hrs. in a Soxhlet apparatus with 250 cc. dry C6H6 and 250 cc. cyclohexane, the extract concentrated to 200 cc., and poured slowly with stirring into 1 l. petr. ether, and the precipitate recrystallized from C6H6-heptane yielded 105 g. Z(Cl, Cl) (II), m. 145° (decomposition). II (40 g.) added during 15 min. in portions to 400 cc. boiling 2N KOH with stirring, the mixture boiled with C, stirred 15 min., filtered, acidified with AcOH, cooled to 30°, and filtered, and the filtrate refrigerated 48 hrs. yielded 24.1 g. Z(HO, Cl) (III), m. above 300°; also obtained in 60% yield by refluxing the Z(MeS, Cl) (IV) with N NaOH. Z(HS, HO) (135 g.) stirred 1 hr. with 100 g. KOH and 3 l. H2O, treated with 115 cc. MeI, stirred 45 min., warmed to 50°, neutralized with AcOH, and filtered gave 120 g. Z(MeS, HO) (V). V (108 g.), 1200 cc. POCl3, and 100cc. PhNMe2 refluxed 1 hr. and worked up in the usual manner yielded 49.5 g. IV, m. 200-1° (decomposition) (PhMe) II (4.0 g.) added at 0° to 5.0 g. KOH, 100 cc. MeOH, and 20 cc. MeSH, the mixture kept 15 min. at 0°, diluted with 50 cc. ice H2O, acidified immediately with AcOH, and filtered gave 3.5 g. IV. Z(HS, Cl) (VI) (5.0 g.) added at 10° to 4.4 g. NaOH in 100 cc. H2O, shaken 10 min. with 6 g. MeI, stirred with C, filtered, acidified with AcOH, and filtered yielded 3.6 g. crude IV. Powd. II (5.0 g.) added at 0° to 200 cc. 0.5N NaOH previously saturated with H2S, stirred 15 min. at 0°, warmed to 10°, treated with C, filtered, acidified with AcOH, and filtered yielded 4.9 g. VI. II (5.0 g.) heated 20 min. on the steam bath with 75 cc. 25% aqueous MeNH2 and filtered hot gave 3.9 g. Z(MeNH, Cl) (VII), m. above 300°, also obtained in 85% yield from IV and aqueous MeNH2. Z(MeO, Cl) (VIII) and aqueous MeNH2 gave 80% VII. II (6.0 g.) added in small portions to 5.0 g. Na in 150 cc. absolute MeOH, warmed, filtered, and evaporated in vacuo, and the residue diluted with 100 cc. H2O, acidified with AcOH, cooled overnight, and filtered gave 4.8 g. VIII, m. 181-2° (C6H6). II (5 g.) and EtONa in EtOH gave similarly Z(EtO, Cl), m. 212-14° (C6H6). IV (2.0 g.) heated 0.5 hr. on the steam bath with 5 g. KOH, 10 cc. MeSH, and 100 cc. H2O, acidified with AcOH, and filtered gave 1.1 g. Z(MeS, MeS) (IX), m. 197-8° (PhMe). II (5.0 g.), 10 g. KOH, 100 cc. H2O, and 15 cc. MeSH heated 4 hrs. on the steam bath, acidified with AcOH, and filtered gave IX. II (5.0 g.) and NaOMe in MeOH refluxed 36 hrs. on the steam bath, concentrated to 50 cc., diluted with 100 cc. H2O, acidified with AcOH, and cooled yielded 3.2 g. Z(MeO, MeO), m. 222-3° (C6H6-EtOH). III (10 g.) and 100 cc. alc. NH3 heated 12 hrs. in a bomb at 200°, cooled, and filtered, the residue dissolved in 300 cc. boiling H2O with concentrated HCl, and the solution adjusted with NH4OH to pH 9 and filtered hot gave 7.6 g. Z(HO, H2N) (X). X (6 g.), 25 g. P2S5, and 300 cc. pyridine refluxed 3 hrs., cooled, and filtered, the residue added to 500 cc. H2O, heated on the steam bath overnight, treated with 50 cc. concentrated NH4OH, heated on the steam bath, cooled, and filtered, and the residue added to 700 cc. boiling H2O, dissolved with concentrated NH4OH, boiled with C, filtered hot, and reprecipitated with AcOH gave 4.1 g. Z(HS, H2N), light green needles, m. above 300°. III (2 g.) and 4.0 g. CS(NH2)2 heated 4 hrs. with 100 cc. absolute EtOH, cooled, and filtered gave Z(HO, HS). Powd. II (5 g.) carefully added to 150 cc. 20-40% aqueous primary amine, heated 10-30 min. on the steam bath, cooled, and filtered gave the corresponding 4-substituted-amino-6-chloropyrazolo[3,4-d]pyrimidine (XI) (method A). The appropriate amine (10-15 g.) in absolute EtOH treated with 5.0 g. II, heated 15-30 min. on the steam bath, cooled, and filtered gave the corresponding XI (method B). By these methods were prepared the following XI (substituent, method of preparation, and % yield given): Me (XII), A, 84; iso-Pr, A, 92; Et, A, 80; Pr, A, 95; iso-Bu, A, 83; PhCH2 (XIII), B, 78; CH2CH2OH, A, 60; cyclohexyl, B, 73; 1-C10H7, B, 70. II (1 g.) and 150 cc. 30% aqueous MeNH2 heated 12 hrs. on the steam bath, treated with more MeNH2, heated again 12 hrs., and cooled overnight gave 0.7 g. Z(MeNH, MeNH) (XIV), m. 248-50° (H2O). Similarly were prepared the following Z(RNH, RNH) (XV) (R, % yield, and m.p. given): Me, 78, 249-50° (EtOH); Et, 85, 238-40° (aqueous EtOH); Bu, 73, 182-3° (aqueous EtOH); Pr, 62, 194-5° (aqueous EtOH); CH2CH2OH, 56, 214-15° (H2O). III (2 g.) and 150 cc. 40% aqueous MeNH2 heated 8 hrs. on the steam bath, treated with an addnl. 100 cc. 40% aqueous MeNH2, and heated again 8 hrs., this treatment repeated once more, and the mixture cooled and filtered gave 62% Z(HO, MeNH). Similarly were prepared the following Z(HO, NRR’)(R, R’, and % yield given): H, Pr, 76 (aqueous EtOH); H, NH2 (hemihydrate), 70 (aqueous EtOH); Me, Me, 67 (aqueous HCONMe2); H, Me2N(CH2)3(di-HCl salt), 86 (EtOH). XIII (2.0 g.) and 100 cc. 30% aqueous Me2NH heated 8 hrs. on the steam bath, treated with 100 cc. aqueous Me2NH, heated 16 hrs., cooled, and filtered gave 1.5 g. Z(PhCH2NH, Me2N), m. 255-6° (EtOH). II (12.0 g.) and 100 cc. absolute alc. NH3 heated 12 hrs. at 100° in a bomb, cooled, and filtered, the residue washed with H2O, suspended in 800 cc. boiling H2O, dissolved by the addition of KOH, boiled 10 min. with C, and filtered hot, and the filtrate acidified with AcOH and filtered yielded 6.4 g. Z(H2N, Cl) (XVI), decompose gradually above 250°. XII (3 g.) and 150 cc. 20% aqueous Me2NH heated 8 hrs. on the steam bath, treated with an addnl. 100 cc. aqueous Me2NH, heated again 8 hrs., filtered, and cooled yielded 1.9 g. Z(MeNH, Me2N) (XVII), m. 272-3° (aqueous EtOH). VIII (2 g.) and alc. NH3 heated 8 hrs. at 100° in a bomb gave 1.1 g. XVI, also obtained under similar conditions from IV. II (5.0 g.), 10 g. CS(NH2)2, and 150 cc. EtOH refluxed 3 hrs. on the steam bath, cooled, and filtered gave 4.1 g. Z(HS, HS) (XVIII). VI (2 g.) and 100 ml. aqueous Me2NH heated 6 hrs. on the H2O bath gave 1.8 g. crude Z(HS, Me2N) (XVIII). Z(HO, Me2N) (3 g.) and 15 g. P2S5 refluxed 6 hrs. with 500 cc. pyridine, and evaporated in vacuo on the steam bath, the residue warmed with 300 cc. H2O on the steam bath, cooled, and filtered, and the residue reprecipitated from hot dilute base with AcOH yielded 0.8 g. XVIII. IV (3 g.) and 100 cc. concentrated NH4OH heated 8 hrs. at 100° in a bomb, cooled, and filtered gave 2.5 g. (crude) Z(H2N, MeS) (XIX), m. 297-8° (EtOH). Z(Cl, MeS) (3 g.), m. 178-9° (decomposition), and 100 cc. concentrated NH4OH yielded similarly 2.6 g. XIX. XIX (1 g.) in 250 cc. boiling H2O and 3 cc. HCl treated with 3 g. NaNO2, heated 10 min. on the steam bath, cooled, and filtered gave 0.4 g. Z(HO, MeS). XIX (1.5 g.), 100 cc. H2O, 10 cc. concentrated HCl, and 10 cc. 30% H2O2 boiled 20 min., neutralized with concentrated NH4OH, and filtered yielded 0.8 g. Z(H2N, HO), Rf 0.036 (PrOHNH4OH), 0.50 (concentrated HCl-iso-PrOH-H2O). VIII (2 g. and 100 cc. 30% aqueous MeNH2 heated 4 hrs. on the steam bath, cooled, and filtered yielded 1.2 g. Z(MeNH, MeS) (XX), m. 253-4° (aqueous EtOH). IX (1.5 g.) and 100 cc. 30% aqueous MeNH2 heated 4 hrs. on the steam bath gave similarly 0.9 g. XX, m. 254-5° (aqueous EtOH). Z(Cl, MeS) (3 g.) and 150 cc. 30% aqueous MeNH2 gave 1.7 g. XX. Z(MeO, MeS) (2 g.) and 130 cc. 30% aqueous Me2NH heated 1 hr. on the steam bath, cooled, and filtered yielded 1.1 g. Z(Me2N, MeS) (XXI), m. 262-5° (aqueous EtOH). IX (1.5 g.) and 100 cc. 30% aqueous Me2NH heated 3 hrs. on the steam bath gave 0.8 g. XXI. II (3 g.), 3 g. NaOH, and 15 cc. EtSH in 100 cc. EtOH kept 0.5 hr. at room temperature, acidified with AcOH, and filtered gave 1.6 g. Z(EtS, Cl), m. 149-50° (C6H6-heptane). Z(HS, H2N) (1 g.) in 30 cc. H2O containing 2.0 g. NaOH stirred 20 min. with 0.5 cc. Me2SO4, acidified with AcOH, and stored gave 0.8 g. Z(MeS, H2N), m. 240-1° (H2O). II (6 g.) and 50 cc. absolute alc. NH3 heated 24 hrs. at 200° in a bomb, the solution evaporated to dryness on the steam bath, the residue dissolved with 5 g. NaOH and 100 cc. H2O, and the solution boiled with C, neutralized with AcOH, filtered, and kept gave Z(H2N, H2N), also obtained similarly from IV or Z(Cl, MeS). The ultraviolet absorption maximum of the various XI and XV are listed. The experimental process involved the reaction of 6-Chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine(cas: 98138-75-1).Application In Synthesis of 6-Chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine

6-Chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine(cas:98138-75-1) belongs to pyrazoles-derivatives. The use of pyrazole derivatives is based on their analgesic, anti-inflammatory, antipyretic, antiarrhythmic, sedative, muscle relaxant, neuroleptic, anticonvulsant, monoamine oxidase inhibitory, antidiabetic and antibacterial activities.Application In Synthesis of 6-Chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

On September 20, 2018, Bandiera, Tiziano; Bertozzi, Fabio; Di Fruscia, Paolo; Sorana, Federico; Berti, Francesco; Rodriguez Gimeno, Alejandra; Caci, Emanuela; Ferrera, Loretta; Pedemonte, Nicoletta; Vicente Galietta, Luis Juan published a patent.Category: pyrazoles-derivatives The title of the patent was Preparation of heterocyclic compounds for the treatment of cystic fibrosis. And the patent contained the following:

The invention relates to compounds of formula I or pharmaceutically acceptable salts or solvates thereof; their preparation an use to modulate CFTR protein or ABC protein activities. Compounds of formula I, wherein R1 is C1-6 alkyl, C3-6 cycloalkyl and hydroxy-C1-6 alkyl; Z is CO and SO2; X1, X2, X3 and X4 are independently CR and N; R is H, C1-6 alkyl, aryl, etc.; R2 is H, C1-6 alkyl, OH, CN, etc.; A1 , A2, A3 and A4 are independently O, CO, SO2, etc.; B is (un)substituted aromatic and heteroaromatic; n and m are independently 0, 1, 2; and pharmaceutically acceptable salts and solvates thereof, are claimed. Example compound II was prepared by cyclocondensation of 3-hydrazinobenzoic acid tert-Bu 4-oxo-3-(2,2,2-trifluoroacetyl)piperidine-1-carboxylate to give 3-[5-tert-butoxycarbonyl-3-(trifluoromethyl)-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-1-yl]benzoic acid, which underwent amidation with N-methyl-1,3-benzodioxol-5-amine hydrochloride to give II. The invention compounds were evaluated for their CFTR modulatory activity. From the assay, it was determined that compound II exhibited EC50 value of < 1 μM. The experimental process involved the reaction of 3-Methyl-1H-pyrazolo[3,4-b]pyridin-5-amine(cas: 1186608-73-0).Category: pyrazoles-derivatives

The Article related to heterocycle preparation cystic fibrosis cftr abc protein modulator, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazoles and other aspects.Category: pyrazoles-derivatives

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

On September 30, 1993, Hichour, M.; Mary, F.; Marzin, C.; Naji, M.; Tarrago, G. published an article.Category: pyrazoles-derivatives The title of the article was N-Alkylation of pyrazolones with OH-protection. And the article contained the following:

The synthesis of biheterocyclic compound I containing two pyrazolone sub-units is described. The oxygen atom of 3-carbethoxypyrazol-5-one is first protected with dihydropyran to obtain selective alkylation with 1-3-dibromopropane. The experimental process involved the reaction of Ethyl 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylate(cas: 153597-59-2).Category: pyrazoles-derivatives

The Article related to pyrazolonecarboxylate protection alkylation dibromopropane, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazoles and other aspects.Category: pyrazoles-derivatives

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics