Tag: M.W:100-200

Related Products of 2075-45-8,Some common heterocyclic compound, 2075-45-8, name is 4-Bromo-1H-pyrazole, molecular formula is C3H3BrN2, 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.

A sealable vessel was charged with potassium carbonate (3.76 g, 27.2 mmol), 4-bromo- lH-pyrazole (4.00 g, 27.2 mmol), and 10 mL DMF. To this mixture, 2-iodopropane (3.27 ml, 32.7 mmol) was added and the vessel sealed. The mixture was heated at 80 C for 16 h and allowed to cool to rt . The mixture was diluted with EtOAc, extracted with water, water, sat NaHCO3, and the organic layer dried over Na2SO4, filtered and evaporated. The mixture was purified via flash chromatography using a EtOAc in CH2C12 gradient. The desired compound (as determined by TLC, 12 stain) was collected as a colorless liquid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1H-pyrazole, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2008/8539; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 5932-27-4, The chemical industry reduces the impact on the environment during synthesis 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, I believe this compound will play a more active role in future production and life.

To a solution of compound G26 (500 mg, 966.07 umol) and compound H22(271 mg, 1.93 mmol) in DML (10 mL) was added CS2CO3 (630 mg, 1.93 mmol). The resulting mixture was heated at 30-40 C and stirred for 16 hr to give yellow solution. LCMS showed the reaction was completed. The mixture was filtered and was partitioned between EtOAc (50 mL). The aqueous layer was extracted with EtOAc (50 mL * 3). The organic layer was washed with saturated brine (50 mL), dried over anhydrous Na2S04, filtered, and concentrated under reduced pressure to give the crude product as a yellow oil. The crude product was purified by combi flash to give compound H23 (490 mg) as a yellow oil.

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, Ethyl 1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; QURIENT CO., LTD.; LEAD DISCOVERY CENTER GMBH; NAM, Kiyean; KIM, Jaeseung; JEON, Yeejin; YU, Donghoon; SEO, Mooyoung; PARK, Dongsik; EICKHOFF, Jan; ZISCHINSKY, Gunther; KOCH, Uwe; (138 pag.)WO2019/197546; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 28466-21-9, name is 1,3,5-Trimethyl-1H-pyrazol-4-amine, molecular formula is C6H11N3, 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. Recommanded Product: 28466-21-9

Step A (1,3,5-trimethyl-pyrazol-4-yl)-isothiocyanate A mixture of 4-amino-1,3,5-trimethylpyrazole (1.32 g, 10.6 mmol) in 50 mL each of CHCl3 and saturated aqueous NaHCO3 was treated dropwise with thiophosgene (0.812 mL, 10.6 mmol) and stirred vigorously for 20 minutes. The layers were separated and the organic phase was washed with brine. After drying (Na2 SO4), the solvent was evaporated in vacuo to provide the title compound (1.8 g, brown oil) suitable for use directly in the next step. NMR (DMSO-d6, 300 MHz): 2.12 (s, 3H, ArCH3), 2.22 (s, 3H, ArCH3), 3.63 (s, 3H, NHCH3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 28466-21-9, its application will become more common.

Reference:
Patent; American Home Products Corporation; US6011053; (2000); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 118430-73-2, name is 3-(tert-Butyl)-1-methyl-1H-pyrazol-5-amine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H15N3

Compound 3B-1 (1.00 g, 4.49 mmol, 1.0 eq), 5-tert-butyl-2-methyl-pyrazol-3-amine (1.38 g, 8.98 mmol, 2.0 eq), Pd2(dba)3 (82.3 mg, 89.8 umol, 0.02 eq), DavePhos (70.7 mg, 180 umol, 0.04 eq) and LiHMDS (1 M, 9.10 mL, 2.0 eq) were taken up into a microwave tube in dioxane (10 mL). The sealed tube was heated at 150 C for 30 min under microwave. TLC (petroleum ether: ethyl acetate = 1:1, Rf = 0.71), LCMS (ET15300-11-P1A, product RT = 0.972), LCMS (ET15300-11-P1B, product RT = 0.973) showed the starting material was consumed completely. The two reaction mixture were combined and concentrated in reduced pressure at 40 C. The residue was purified by silica gel chromatography (100-200 mesh silica gel), eluted with petroleum ether: ethyl acetate (80: 1~ 0: 1) to afford compound 3C-2 (1.00 g, 2.95 mmol, 32.8 %yield) as yellow solid. NMR: ET15300-11-P1A 400 MHz CDC1 delta 8.16 (d, J = 6.0 Hz, 1H), 7.90 (d, J = 8.4 Hz, 1H), 7.45 (d, J = 8.8 Hz, 1H), 7.01 (d, J = 6.0 Hz, 1H), 6.08 (s, 1H), 3.72 (s, 3H), 2.55 (s, 3H), 1.34 (s, 9H).

According to the analysis of related databases, 118430-73-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LUTRIS PHARMA LTD.; SHELACH, Noa; (76 pag.)WO2019/26065; (2019); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

175277-11-9, name is 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C9H14N2O2

3-tert-butyl-1-methyl-1H-pyrazole-5-carboxylic acid (0.090 g, 0.49 mmol) was dissolved in CH2Cl2 (5 mL). DMAP(0.005 g, 0.04 mmol) and EDC (0.163 g, 0.85 mmol) were added, and the mixture was stirred for15 min at room temperature. The TFA salt was suspended in CH2Cl2 (3 mL) and treated withtriethylamine (136 muL, 0.98 mmol) at 0C. The resulting mixture was dropwise combined withthe activated acid and stirred for 18 h at room temperature. The solvent was evaporated under reduced pressure. The residue was treated with H2O and extracted with ethyl acetate (3 × 10 mL).The combined organic layers were washed with sat. NaHCO3 (3 × 10 mL), H2O (20 mL), andbrine (20 mL). The solvent was dried over MgSO4 and removed under reduced pressure. Thecrude residue was purified by silica column chromatography using EtOAc as eluent to obtain C(33 % yield).

The synthetic route of 175277-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Silva, Daniel G.; Ribeiro, Jean F.R.; De Vita, Daniela; Cianni, Lorenzo; Franco, Caio Haddad; Freitas-Junior, Lucio H.; Moraes, Carolina Borsoi; Rocha, Josmar R.; Burtoloso, Antonio C.B.; Kenny, Peter W.; Leitao, Andrei; Montanari, Carlos A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 22; (2017); p. 5031 – 5035;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 139756-02-8, A common heterocyclic compound, 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, molecular formula is C8H14N4O, 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.

General procedure: We intended to synthesize compounds based on 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one scaffold by using microwave assisted protocol (Scheme 1). In this direction we started the studies for optimization of synthesis of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 3a. The optimization studies were initiated by screening of different oxidizing agents as depicted in Table1, see Supplementary data using DMSO:Water in 1:1 proportion to see the conversion in desired product. Amongst all oxidants, the best result was observed with K2S2O8, in equivalence studies for catalyst, 3eq. of catalyst has given maximum yields (Table1, see Supplementary data). Therefore, all reactions were conducted using this condition after optimization of catalyst. However, oxone has also given the product 3a with minor yields. After screening of the catalyst we started study of selectivity for solvent that could affect the formation of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 3a. The solvent screening was carried out to find out the best conversion, the mixture of DMSO:H2O in 1:1 proportion has given the best results with excellent yields (Table2, see Supplementary data). The microwave protocols were optimized for this reaction as mentioned in Table 3, see Supplementary data; the reactions carried under different microwave Watt powers have given varied results. Wherein, entry 3(b) (Table3, see Supplementary data) was found to be the best condition for maximum conversion. A series of compounds based on 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one scaffold was synthesized using these optimized conditions, wherein, all kind of substrates with diversity around aryl ring were chosen for conversion and in all cases products obtained in good to excellent yields (Table1).

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; Reddy, G. Lakshma; Guru, Santosh Kumar; Srinivas; Pathania, Anup Singh; Mahajan, Priya; Nargotra, Amit; Bhushan, Shashi; Vishwakarma, Ram A.; Sawant, Sanghapal D.; European Journal of Medicinal Chemistry; vol. 80; (2014); p. 201 – 208;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 96799-02-9, A common heterocyclic compound, 96799-02-9, name is 5-(Furan-2-yl)-1H-pyrazol-3-amine, molecular formula is C7H7N3O, 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.

6- amino-benzothiazole (188 mg, 1.25 mmol) and DIPEA (0. 22 mL, 1.25 mmol) were added to a solution of cyanuric chloride (230 mg, 1.25 mmol) in THF (16 mL) at 0 0C. The reaction mixture was stirred at 0 0C to room temperature for 2 hours. 3-amino-5-(2- furyl) pyrazole (187 mg, 1.25 mmol) and DIPEA (0.22 mL, 1.25 mmol) were added to the above mixture and the resulting mixture was heated with microwave initiator at 150 C for 10 minutes. 1 -methylpiperazine (0.28 mL, 2.50 mmol) and DIPEA (0.44 mL, 2.50 mmol) were added to the mixture and the mixture was heated with microwave initiator at 60 0C for 10 minutes. Saturated NaHCO3 in water was added and the mixture was extracted by ethyl acetate (3 x 50 mL). The combined organic was washed by brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a silica gel column and eluted with 0- 5 % MeOH/DCM which afforded compound 37 as a white solid (200 mg, 34%). 1H NMR (400 MHz, DMSO-d6) delta 12.86 (bs, IH, NH), 10.99 (bs, IH, NH), 9.61 (bs, IH, NH), 9.21 – 6.59 (m, 8H, Ar-H), 4.68 (bs, 2H, CH2), 3.43 (bs, 2H, CH2), 3.09 (bs, 4H, 2CH2), 2.76 (s, 3H, CH3); ESI-MS: calculated for (C22H22Ni0OS) 474, found 475 [M+H]+. HPLC: retention time: 14.52 min. purity: 97%.

The synthetic route of 96799-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABRAXIS BIOSCIENCE, LLC; TAO, Chunlin; WANG, Qinwei; NALLAN, Laxman; POLAT, Tulay; HO, David; DESAI, Neil, P.; WO2010/144550; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C5H6N2O2

1) N-methoxy-N,1-dimethyl-1H-pyrazol-5-carboxamide N,O-dimethylhydroxylamine hydrochloride (1.30 g) was added to an N,N-dimethylformamide (32 mL) solution that contained 1-methyl-1H-pyrazol-5-carboxylic acid (1.21 g), O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (4.38 g) and diisopropylethylamine (3.34 mL) at a room temperature, and the obtained solution was then stirred for 2 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was washed with water and a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, chloroform_methanol=100:0 to 95:5), so as to obtain the title compound (1.03 g) in the form of a yellow oily substance. 1H NMR (200 MHz, CHLOROFORM-d) delta ppm 3.36 (s, 3H) 3.66 (s, 3H) 4.13 (s, 3H) 6.77 (d, J=2.20 Hz, 1H) 7.48 (d, J=2.20 Hz, 1H); MS (ESI pos.) m/z: 170 [M+H]+

The synthetic route of 16034-46-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Nakamura, Toshio; Sakagami, Kazunari; Konishi, Kazuhide; Yamamoto, Kanako; Masuda, Seiji; Matsuda, Yohei; Okada, Kumiko; Shibata, Tsuyoshi; Ohta, Hiroshi; Yasuhara, Akito; Kawamoto, Hiroshi; Amada, Hideaki; Urabe, Hiroki; Nishikawa, Rie; Kashiwa ASHIWA, Shuhei; US2013/137865; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 3524-32-1, 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. 3524-32-1, name is 5-Amino-1,3-dimethylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Electrolysis was carried out usinga B5-49 direct current source, 0.2 m aqueous NaOH as the supportingelectrolyte, in a glass temperature-controlled (25 C) cell (V = 150 ml)with a NiO(OH) anode (S = 48 cm2) prepared by a reported procedure36and a Ti cathode (S = 20 cm2). The supporting electrolyte (100 ml) andamine 1a-e (0.003 mol) were placed into the cell and electrolysis wascarried out at a current of 290 mA. Once a 2 F per mole of the startingamine was passed (Q = 579 C), electrolysis was stopped. The reactionmixture was stirred for more 0.5 h in the absence of current and analyzedby TLC with light petroleum-ethyl acetate (1:1) as the eluent. ConcentratedHCl was then added to the reaction mixture to pH ~ 3 andthe mixture was extracted with CHCl3 (3×50 ml). The extracts werecombined, dried with anhydrous MgSO4 and concentrated in vacuo.Column chromatography on SiO2 with light petroleum-ethyl acetate(10:1) as the eluent gave azopyrazoles 2a-e which were identified usingthe reported characteristics.26,28 The aqueous solution that remainedafter extraction (see above) was concentrated in vacuo and NaOH wasadded with stirring (to pH ~ 10). The nonreacted starting amines 1a-ewere extracted with CHCl3 (3×30 ml) and identified by TLC and 1H NMR.

The synthetic route of 5-Amino-1,3-dimethylpyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lyalin, Boris V.; Sigacheva, Vera L.; Kokorekin, Vladimir A.; Petrosyan, Vladimir A.; Mendeleev Communications; vol. 25; 6; (2015); p. 479 – 481;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 5775-86-0, The chemical industry reduces the impact on the environment during synthesis 5775-86-0, name is 4-Bromo-1,5-dimethylpyrazole, I believe this compound will play a more active role in future production and life.

To compound 264.4(5.Og, l6mmol, 1.Oeq) and 4- bromo-1,5-dimethyl-1H-pyrazole (2.74g, l4mmol, 0.84eq) in 1,4-dioxane (4OmL), potassium carbonate (6.96g, 48mmol, 3.Oeq) was added. Argon gas was purged through the reaction for 10- 1 5mm. Then, [1,1 ?-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)] complex with CH2C12 (0.41g, 0.48mmol, 0.O3eq) was added. Reaction mixture was stirred at 100-110 C for 3h. After completion of the reaction, the reaction mixture was transferred to water and extracted with ethyl acetate. Organic layers were combined, dried over anhydrous Na2SO4, filtered and evaporated under vacuum to obtain 264.5 (1.5g, 33.6%). MS(ES): m/z 266.37 [M+H]t

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, 4-Bromo-1,5-dimethylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NIMBUS LAKSHMI, INC.; GREENWOOD, Jeremy Robert; LEIT DE MORADEI, Silvana Marcel; MASSE, Craig E.; MCLEAN, Thomas H.; MONDAL, Sayan; (869 pag.)WO2018/75937; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics