Research on new synthetic routes about 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid

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.

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