Category: 31728-75-3

Electric Literature of 31728-75-3, A common heterocyclic compound, 31728-75-3, name is 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid, molecular formula is C6H8N2O2, 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.

Under an atmosphere of argon, diisopropylethylamine (3.49 ml) and diphenylphosphoryl azide (2.37 ml) were added in turn to a stirred mixture of 1,5-dimethyl-1H-pyrazole-4-carboxylic acid (1.4 g), tert-butanol (4 ml) and 1,4-dioxane (40 ml) and the reaction mixture was stirred at ambient temperature for 10 minutes. The resultant mixture was heated to 110 C. for 3 hours. The solvent was evaporated and the reaction product was purified by column chromatography on silica using ethyl acetate as the eluent. There was thus obtained 4-(tert-butoxycarbonylamino)-1,5-dimethyl-1H-pyrazole (0.225 g); 1H NMR: (DMSOd6) 1.4 (s, 9H), 2.2 (s, 3H), 3.55 (s, 1H), 6.0 (br s, 1H), 9.3 (br s, 1H).

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:
Patent; Jung, Frederic Henri; Morgentin, Remy Robert; Ple, Patrick; US2009/76075; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 31728-75-3,Some common heterocyclic compound, 31728-75-3, name is 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid, molecular formula is C6H8N2O2, 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.

mixture of 4-(6-(4-amino-4-methylpiperidin-l-yl)pyridin-3-yl)-6-(2-hydroxy-2- methylpropoxy)pyrazolo[l,5-a]pyridine-3-carbonitrile dihydrochloride (Intermediate P46; 50 mg, 0.12 mmol), HATU (54 mg, 0.14 mmol), l,5-dimethyl-lH-pyrazole-4-carboxylic acid (25 mg, 0.18 mmol) in DCM (2.4 mL) was treated with DIEA (104 mu,, 0.59 mmol) and then stirred for 16 h at ambient temperature. The reaction mixture was diluted with DCM and washed with saturated NaHCCb. The organic extracts were dried over anhydrous Na2S04(s), filtered and concentrated in vacuo. The reaction was purified by silica chromatography (1-10% MeOH in EtOAc as the gradient eluent) to cleanly provide the title compound (41.9 mg, 63.2% yield) MS (apci) m/z= 543.20 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid, its application will become more common.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COLLIER, James; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; RAMANN, Ginelle A.; TANG, Tony P.; REN, Li; WALLS, Shane M.; (946 pag.)WO2018/71454; (2018); A1;,
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. 31728-75-3, name is 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., category: pyrazoles-derivatives

To a suspension of 6-(2-amino-5-chlorothiazol-4-yl)-3,4-dihydroquinolin-2(1H)-one (0.100 g, 0.41 mmol) and 1,5-dimethyl-1H-pyrazole-4-carboxylic acid (0.063 g, 0.22 mmol), and DIPEA (0.16 mL, 0.51 mmol in acetonitrile (5 mL) in a sealed tube was added propylphosphonic anhydride solution (50 wt % in ethyl acetate, 0.61 mL, 0.1.02 mmol). The sealed tube was heated to 100 C. for 16 h. The resulting mixture was cooled to room temperature, and partitioned between EtOAc (50 mL) and 50 mL of water. The organic layer was separated and the aqueous layer was extracted with EtOAc (3*25 mL). The combined organic layers were washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography by 0-5% methanol-dichloromethane to give 1,5-dimethyl-N-(4-(2-oxo-1,2,3,4-tetrahydroquinol in-6-yl)thiazol-2-yl)-1H-pyrazole-4-carboxamide (0.044 g, 30%). 1H NMR (400 MHz, DMSO-d): delta 12.21 (bs, 1H), 10.18 (s, 1H), 8.30 (s, 1H), 7.74 (m, 1H), 7.69 (dd, 1H, J=8.4, 2.0 Hz), 7.44 (s, 1H), 6.90 (d, 1H, J=8.0 Hz), delta, 3.77 (s, 3H), 2.93 (t, 2H, J=7.2 Hz), 2.91 (s, 3H), 2.50 (partial masked under d-DMSO, m, 2H); MS (ESI): Calcd. For C18H17N5O2S: 367, found 368 (M+1)+.

According to the analysis of related databases, 31728-75-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nantbio, Inc.; Tao, Chunlin; Nallan, Laxman; Ho, David G.; Wang, Qinwei; Weingarten, Paul; Juncker-Jensen, Anna B.; (121 pag.)US2018/201610; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 31728-75-3, A common heterocyclic compound, 31728-75-3, name is 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid, molecular formula is C6H8N2O2, 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.

The 1.60g of 1,5-dimethyl -1H- pyrazole-4-carboxylic acid, 1.23 g of oxalyl chloride, approximately 15mg of N, N- dimethylformamide and 50mL of tetrahydrofuran was stirred at 25 1 hour. The reaction mixture was concentrated under reduced pressure to give 1,5-dimethyl -1H- pyrazole-4-carbonyl chloride.The 2.34 g of aluminum chloride in a mixture of 3.42g of sodium azide, and 50mL of tetrahydrofuran was stirred with heating under reflux for 2 hours. After ice-cooling the reaction mixture, the 1,5-dimethyl -1H- pyrazole-4-carboxamido mixture was added to the reaction mixture, followed by heating and stirring at reflux for 3 days. After cooling, the reaction mixture was added to 5.27g of sodium nitrite and a mixture of 100mL of water while stirring. The mixture was acidified with concentrated hydrochloric acid and then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to give 1.6g of 1- (1,5-dimethyl -1H- pyrazol-4-yl) -1,4-dihydro-tetrazole – 5-one.

The synthetic route of 31728-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Co., Ltd.; Dong, Xiuping; Gao, Qiaohuangshu; (181 pag.)CN105636955; (2016); 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. 31728-75-3, name is 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 31728-75-3

To a 0C solution of 1 ,5-dimethyl-lH-pyrazole-4-carboxylic acid (1.0 g, 7.14 mmol) in DCM/MeOH (7 mL each) was added 2M TMSCHN2 in hexane (4.28 mL, 8.56 mmol). The reaction mixture was stirred at 0C for 1 h, then was allowed to warm to RT and stirred at RT overnight, then was concentrated in vacuo. The crude product was chromatographed (80 g Si02; continuous gradient from 0% to 50% EtOAc in hexane over 20 min) to give the title compound (900 mg, 5.84 mmol, 82 % yield). LCMS, [M + H]+ = 155.2.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 31728-75-3.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHENG, Peter Tai Wah; LI, Jun; SHI, Yan; WANG, Ying; ZHANG, Hao; KENNEDY, Lawrence J.; WALKER, Steven J.; REDDIGUNTA, Ramesh Babu; (138 pag.)WO2019/126098; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

31728-75-3, name is 1,5-Dimethyl-1H-pyrazole-4-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. Recommanded Product: 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid

To a 0C solution of 1 ,5-dimethyl- lH-pyrazole-4-carboxylic acid (1.0 g, 7.14 mmol) in DCM/MeOH (7 mL each) was added 2M TMSCHN2 in hexane (4.28 mL, 8.56 mmol). The reaction mixture was stirred at 0C for 1 h, then was allowed to warm to RT and stirred at RT overnight, then was concentrated in vacuo. The crude product was chromatographed (80 g Si02; continuous gradient from 0% to 50% EtOAc in hexane over 20 min) to give the title compound (900 mg, 5.84 mmol, 82 % yield). LCMS, [M + H]+ = 155.2.

The synthetic route of 31728-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; CHENG, Peter Tai Wah; WANG, Ying; (140 pag.)WO2019/126085; (2019); A1;,
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. 31728-75-3, name is 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H8N2O2

The 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide was prepared from 3-nitrobenzoyl chloride using the following multiple step procedure: Step 1: 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide.; A dry flask was charged with 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid (0.144 g, 1.03 mmol) and thionyl chloride (5 mL) and allowed to stir at 79 C. for 3 h. The thionyl chloride was then removed by concentration in vacuo. The crude acid chloride was cooled to room temperature, and then dissolved in THF (101 mL). 6-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 40, 0.260 g, 1.03 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux overnight. The reaction mixture was then allowed to cool to room temperature and filtered. The solid residue was washed with 0 C. THF and collected to afford the 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide as a solid (0.177 g, 0.47 mmol, 46%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 31728-75-3.

Some common heterocyclic compound, 31728-75-3, name is 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid, molecular formula is C6H8N2O2, 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. Quality Control of 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid

The 4-amino-l,5-dimethyl-lH-pyrazole used as a starting material was prepared as follows :-Under an atmosphere of argon, diisopropylethylamine (3.49 ml) and diphenylphosphoryl azide (2.37 ml) were added in turn to a stirred mixture of 1 ,5-dimethyl-l/J-pyrazole-4-carboxylic acid (1.4 g), fer/-butanol (4 ml) and 1,4-dioxane (40 ml) and the reaction mixture was stirred at ambient temperature for 10 minutes. The resultant mixture was heated to 110C for 3 hours. The solvent was evaporated and the reaction product was purified by column chromatography on silica using ethyl acetate as the eluent. There was thus obtained 4-(fert-butoxycarbonylamino)- 1,5 -dimethyl- lH-pyrazole (0.225 g); 1H NMR: (DMSOd6) 1.4 (s, 9H), 2.2 (s, 3H), 3.55 (s, IH), 6.0 (br s, IH), 9.3 (br s, IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 31728-75-3, its application will become more common.