Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 1018446-95-1, name is tert-Butyl 4-amino-1H-pyrazole-1-carboxylate, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1018446-95-1, Safety of tert-Butyl 4-amino-1H-pyrazole-1-carboxylate

[0607j To a solution of N-(4-(2-chloropyrimidin-4-yl)-2-methylbenzyl)-3 – isopropoxyazetidine-1-carboxamide (220 mg, 0.60 mmol) and tert-butyl 4-amino-1H-pyrazole- 1-carboxylate (132 mg, 0.72 m mol) in dry 1,4-dioxane (8 mL) was added Pd2(dba)3 (55 mg,0.06 mmol), S-phos (49 mg, 0.12 mmol) and Cs2CO3 (390 mg, 1.2 mmol). The mixture was stirred at 120 C for 4 h under N2. After cooling to rt, the mixture was diluted with EtOAc (150 mL) and washed with water (60 mL x 2). The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The residue was dissolved in 3 N HC1 in MeOH (10 mL) and the resulting mixture was stirred at rt for 1 h. After concentration in vacuo, the residue was purified by prepHPLC (CH3CN/H20 with 0.05% NH4OH as mobile phase) to give N-(4-(2-((1H-pyrazol-4- yl)amino)pyrimidin-4-yl)-2-methylbenzyl)-3 -isopropoxyazetidine- 1 -carboxamide as a white solid (88 mg, yield: 35%). ESI-MS (M+H) : 544.2. ?H NMR (400 MHz, CD3OD) 5: 8.38 (d, J= 4.8 Hz, 1H), 8.05 (s, 1H), 7.91-7.90 (m, 2H), 7.75 (s, 1H), 7.37 (d, J= 8.4 Hz, 1H), 7.16 (d, J5.2 Hz, 1H), 4.42-4.36 (m, 3H), 4.18-4.14 (m, 2H), 3.81-3.78 (m, 2H), 3.67-3.61 (m, 1H), 2.41 (s, 3H), 1.14 (d, J 6.0 Hz, 6H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, tert-Butyl 4-amino-1H-pyrazole-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; MA, Bin; CHAN, Timothy, Raymond; SUN, Lihong; ZHANG, Lei; KUMARAVEL, Gnanasambandam; LYSSIKATOS, Joseph, P.; KOCH, Kevin; MIAO, Hua; WO2015/89337; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1031351-95-7, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1031351-95-7, name is Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 3-formyl-l-methyl-lH-pyrazole-5-carboxylate (Bellen Chem;l g, 5.95 mmol) in CH2CI2 (30 mL) at 0 C was added bis-(2-methoxyethyl)aminosulfur-trifluoride (3.29 mL, 17.8 mmol) in CH2CI2 (5 mL) dropwise via syringe pump over 40 minutes. The mixture was allowed to stir at 0 C for 20 minutes, then the ice-bath was removed, and the mixture was allowed to warm to ambient temperature. The mixture was then allowed to stir for an additional 90 minutes and was quenched by slow addition of saturated, aqueous NaHC( (25 mL) added via syringe pump over 1 hour. The mixture was diluted with CH2CI2 (15 mL), then the layers were separated, and the aqueous layer was extracted with CH2CI2 (3 x 7 mL). The combined organic fractions were dried over anhydrous Na2S04, filtered, and concentrated under reduced pressure. The residue was purified via column chromatography (S1O2, 50% ethyl acetate/heptanes) to give the title compound (1.01 g, 5.31 mmol, 89% yield). MS (ESI+) m/z 191 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; PLIUSHCHEV, Marina, A.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; SWEIS, Ramzi, Farah; DART, Michael, J.; RANDOLPH, John, T.; MURAUSKI, Kathleen; (674 pag.)WO2019/90076; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 138786-86-4, name is Methyl 4-nitro-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 138786-86-4

PART I: Synthesis Scheme I, shows that 4-nitro-1H-pyrazole-3-carboxylic acid (compound 12) was alkylated with methyl iodide in the presence of potassium carbonate in DMF. After flash chromatography on silica gel, two regioisomers, alkyl 1-alkyl-4-nitro-1H-pyrazole-3-carboxylate (compound 13a, 1,3-isomer) and alkyl 1-alkyl-4-nitro-1H-pyrazole-5-carboxylate (compound 13b, 1,5-isomer) were obtained in 26% and 74% yield, respectively. The structures of the isomers (compounds 13a, 13b) were determined by NOESY analysis: a NOESY correlation was observed between H-5 and alkyl protons in compound 13a.16 The nitro group of compounds 13a and 13b was reduced by hydrogenation in the presence of a catalytic amount of catalytic amount of 10% Pd/C to produce amines compounds 14a and 14b, respectively. Cyclization of compound 14b with urea afforded compound 15. Chlorination of compound 15 with POCl3 and DIPEA in toluene afforded compound 16 in 68% yield. Treatment with appropriate substituted anilines in isopropanol with 1 drop of conc. HCl with compound 16, provided the instant compounds 4-11 of this invention (65-78% yields).

The synthetic route of 138786-86-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Duquesne University of the Holy Spirit; Gangjee, Aleem; (26 pag.)US2019/276457; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 59843-75-3, name is 3-(p-Tolyl)-1H-pyrazole, molecular formula is C10H10N2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 59843-75-3

Production Example 143 3-p-Tolyl-1-trityl-1H-pyrazole 6.94 g of the title compound was obtained as pale brown crystals from 4.59 g 3-p-tolyl-1H-pyrazole (compound in Production Example 126) by the same method as in Production Example 15.1H-NMR (CDCl3) delta: 2.35(s, 3H), 6.50(d, J=2.4Hz, 1H), 7.16(d, J=8.0Hz, 2H), 7.21(m, 6H), 7.27 (d, J=2. 4Hz, 1H), 7.30(m, 9H), 7.69(d, J=8.0Hz, 2H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59843-75-3, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; EP1382603; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 3112-31-0, name is 1H-Pyrazole-3,5-dicarboxylic acid, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Application In Synthesis of 1H-Pyrazole-3,5-dicarboxylic acid

1H-Pyrazole-3,5-dicarboxylic acid (200 mg, 1.281 mmol), methanamine (2M in THF, 0.705 mL, 1.409 mmol) and HATU (536 mg, 1.409 mmol) were combined in DMF (2 mL). DIPEA (0.448 mL, 2.56 mmol) was added and reaction mixture stirred at rt. under N2 for 2 h. The reaction mixture was concentrated to dryness and used crude for the next step. (0432) LCMS (2 min Formic): Rt = 0.37 min, [MH]+ = 183.1.

The synthetic route of 1H-Pyrazole-3,5-dicarboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; LIWICKI, Gemma Michele; LUCAS, Simon Christopher Cranko; PRESTON, Alexander G; SEAL, Jonathan, Thomas; WALL, Ian David; WATSON, Robert J; (0 pag.)WO2018/158212; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 72760-85-1, name is 3-Amino-5-(methylthio)-1H-pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 72760-85-1

General procedure: A mixture of pyrazole-imines 7 (1 mmol), aldehyde (1 mmol), TMSCN (1.2 mmol) in [Bmim]BF4 (0.5 g) was heated at 120 C for 24 h. After cooling, the reaction mixture was washed with water (5 mL) and the residue washed with MeOH to afford pure product 8.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Goli, Shokoufe; Mirzaei, Peiman; Bazgir, Ayoob; Journal of the Iranian Chemical Society; vol. 15; 12; (2018); p. 2803 – 2809;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 78208-72-7, name is Ethyl 3-isopropyl-1H-pyrazole-5-carboxylate, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 78208-72-7, Formula: C9H14N2O2

Preparation 14 5-ISOPROPYL-1-R2- (TETRAHVDRO-PVRAN-2-YLOXV)-ETHYLL-1 H-PYRAZOLE-3-CARBOXYLID ethyl ester The ester of preparation 6 (509mg, 2. 8MMOL), 2- (2-bromoethoxy) tetrahydro-2H- pyran (732mg, 3. 5MMOL) and potassium carbonate (483mg, 3. 5MMOL) were dissolved in 1-methyl-2-pyrrolidinone (5mL) and the reaction mixture heated to 80°C for 18 hours. The reaction mixture was cooled, poured into ethyl acetate, washed with water (x 2) and brine, dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with pentane: ethyl acetate 80: 20 to 60: 40 to yield the title product, 663mg (76percent). HNMR (CD3, 400MHZ) : 1.25 (d, 6H), 1.37 (t, 3H), 1.44-1. 71 (m, 6H), 2.97 (m, 1 H), 3.42 (m, 1 H), 3.54 (m, 1 H), 3.75 (m, 1 H), 4.00 (m, 1 H), 4.32 (m, 2H), 4.54 (t, 1 H), 4.68 (m, 1 H), 4.76 (m, 1 H), 6.64 (s, 1 H). MS ES+ M/Z 227 [MH] +

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/9965; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 180207-57-2, name is 2-(1H-Pyrazol-4-yl)ethanol belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C5H8N2O

General procedure: To a mixture of 3,6-dichloropyridazine (3.73 g, 25 mmol), 4(5)-Hydroxymethylimidazole (1.96 g, 20 mmol), and Cs2CO3 (8.14 g, 25 mmol) was added acetonitrile (80 mL). The mixture was refluxed for 3 h and was poured into H2O (200 mL). 1N HCl(aq) was added slowly until the pH is ca. 7-8. Then the aqueous layer was extracted with EtOAc (150 mL) and then CH2Cl2 (100 mL x 5). The combined organic layer was dried (Na2SO4) and filtered. After removal of solvent, the product was triturated with 10% CH2Cl2/Et2O (30 mL x 3) to give 1.74 g of product. The filtrate was concentrated and was purified by column using 60-70-80% EtOAc/(CH2Cl2/hexane=1/1) as the eluent to give 629 mg of prouct. Total 2.36g of D (53%) was obtained.

The synthetic route of 180207-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Shyh-Ming; Tang, Yuting; Rano, Thomas; Lu, Huajun; Kuo, Gee-Hong; Gaul, Michael D.; Li, Yaxin; Ho, George; Lang, Wensheng; Conway, James G.; Liang, Yin; Lenhard, James M.; Demarest, Keith T.; Murray, William V.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 5; (2014); p. 1437 – 1441;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 82668-50-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 82668-50-6, name is Ethyl 2-(3-Pyrazolyl)acetate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Ethyl 2-(1H-pyrazol-3-yl)acetate (180 mg, 1.17 mmol), caesium carbonate (762 mg, 2.34 mmol) and N,N-dimethylformamide (2 mL) were added in a 25 mL single-neck flask. After cooling in an ice bath, methyl iodide (332 mg, 2.34 mmol) was added dropwise, and the reaction was continued for 2 hours in an ice bath. After completion of the reaction monitored by TLC, water (20 mL) was added. Then mixture was extracted with ethyl acetate (3?10 mL), and the organic layers were combined and dried over anhydrous sodium sulfate. Solvent was removed in vacuo to afford a mixture of ethyl 2-(1-methyl-1H-pyrazol-3-yl)acetate and ethyl 2-(1-methyl-1H-pyrazol-5-yl)acetate (yellow oil, 136 mg). Step 5: 2-(1-Methyl-1H-pyrazol-5-yl)acetic acid and 2-(1-methyl-1H-pyrazol-3-yl)acetic acid (0079) The mixture of ethyl 2-(1-methyl-1H-pyrazol-3-yl)acetate and ethyl 2-(1-methyl-1H-pyrazol-5-yl)acetate (136 mg, 0.81 mmol), lithium hydroxide monohydrate (102 mg, 2.43 mmol) and ethanol/H2O (2 mL/0.5 mL) were added in a 25 mL single-neck flask, and the mixture was reacted at room temperature for 0.5 hour. After completion of the reaction, ethanol was removed under reduced pressure, then water (2 mL) was added. The mixture was adjusted to pH 3 with 1N hydrochloric acid and extracted with ethyl acetate (3 10 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo to remove the solvent to give a product (yellow oil, 100 mg). Step 6: Synthesis of N-(2,6-dichloro-3′-cyano-4′-isobutyl-[1,1′-biphenyl]-4-yl)-2-(1-methyl-1H-pyrazol-3-yl)acetami de (9A) and N-(2,6-dichloro-3′-cyano-4′-isobutyl-[1,1′-biphenyl]-4-yl)-2-(1-methyl-1H-pyrazol-5-yl)acetami de (9B) (0080) 4′-Amino-2′,6′-dichloro-4-isobutyl-[1,1′-biphenyl]-3-carbonitrile (40 mg, 0.13 mmol), the mixture of 2-(1-methyl-1H-pyrazol-5-yl)acetic acid and 2-(1-methyl-1H-pyrazol-3-yl)acetic acid (44 mg, 0.32 mmol), HATU (118 mg, 0.38 mmol), N,N-diisopropylethylamine (50 mg, 0.39 mmol) and dichloromethane (2 mL) were added in a 25 mL single-neck flask, and the mixture was reacted at room temperature for 4 hours. The resulting crude product was separated by preparative thin layer chromatography (petroleum ether: ethyl acetate = 1:1) to give N-(2,6-dichloro-3′-cyano-4′-isobutyl-[1,1′-biphenyl]-4-yl)-2-(1-methyl-1H-pyrazol-3-yl)acetami de (white aolid, 26 mg), 1H NMR (400 MHz, CDCl3) delta 9.23 (s, 1H), 7.66 (s, 2H), 7.47 (s, 1H), 7.33 (t, J = 7.4 Hz, 4H), 6.19 (s, 1H), 3.93 (s, 3H), 3.75 (s, 2H), 2.75 (d, J = 7.3 Hz, 2H), 2.02 – 1.97 (m, 1H), 0.97 (d, J = 6.6 Hz, 6H). MS (ESI) m/z: 441.0 (M+1) and N-(2,6-dichloro-3′-cyano-4′-isobutyl-[1,1′-biphenyl]-4-yl)-2-(1-methyl-1H-pyrazol-5-yl)acetami de (white aolid, 27 mg), 1H NMR (400 MHz, CDCl3) delta 8.26 (s, 1H), 7.63 (s, 2H), 7.47 (d, J = 3.3 Hz, 2H), 7.34 (s, 2H), 6.26 (s, 1H), 3.87 (s, 3H), 3.80 (s, 2H), 2.75 (d, J = 7.3 Hz, 2H), 1.97 – 1.88 (m, 1H), 0.97 (d, J = 6.6 Hz, 6H). MS (ESI) m/z: 440.9 (M+1).

The synthetic route of Ethyl 2-(3-Pyrazolyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fudan University; WANG, Yonghui; HUANG, Yafei; QIU, Ruomeng; TANG, Ting; (68 pag.)EP3581561; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 368870-03-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 368870-03-5, name is (4-(1H-Pyrazol-1-yl)phenyl)methanamine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

4-(Pyrazol-1-yl)benzylamine (12.2 g, 0.07 mol) was dissolved in 50 mL of 2-methoxyethanol (75 mL) and 3-isopropyl-pyrimidine-5,7-dithiol (2) (13.3 g, 0.059 mol) was added under an atmosphere of nitrogen. The reaction mixture was heated at 120 C for 12 hours. The reaction product crystallized upon cooling to 10-15 C and was filtered off. After washing with 2-methoxyethanol, then THF, and drying in vacuo at 75 C, 13.7 g of product are obtained in 62% yield. The analytical sample was recrystallized from DMS0/H20, dried at 75 C under vacuum; m.p. 268-270 C (decomposition), UV (nm): 268 l, 288 l, 300 l, 336 l?. MS ESI+ 366.1 (M+H)+, ESI- 364.1 (M-H) . NMR (500 MHz; DMSO-d6): 1.23 (d, / = 7.03 Hz, 6H, -CH(C//3)2); 3.44 (bs, 1H, -C//(CH3)2); 4.75 (d, J = 6.11 Hz, 2H, -NH-G-); 6.50-6.51 (m, 1H, HAT); 7.46 (d, / = 7.95 Hz, 2H, HAT); 7.71 (d, / = 1.53 Hz, 1H, HAT); 7.79 (d, J = 8.25 Hz, 2H, HAT) ; 8.45 (d, J = 2.45 Hz, 1H, HAT) ; 9.17 (bs, 1H, -NH-); l2.23(bs, 1H, -NH); 13.74 (bs, 1H, -SH). 13C (125 MHz; DMSO-d6): 21.8; 42.4; 107.7; 118.3; 127.6; 128.7; 138.7; 140.8. Anal. (CI8H19N7S) C, H, N, S.

The synthetic route of (4-(1H-Pyrazol-1-yl)phenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERZITA PALACKEHO V OLOMOUCI; USTAV EXPERIMENTALNI BOTANIKY AV CR, V.V.I.; HAVLICEK, Libor; STURC, Antonin; REZNICKOVA, Eva; JORDA, Radek; KRYSTOF, Vladimir; STRNAD, Miroslav; (66 pag.)WO2019/149295; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics