In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 25016-20-0 as follows. Quality Control of 1-Methyl-1H-pyrazole-3-carboxylic acid
Compound 1007; (2R.6S, 12Z, 13aS, 14aR, 16aS)-2-{[7-methoxy-8-methyl-2-(propan-2-yloxy)quinolin-4- yl]oxy}-N-[(1-methylcyclopropyl)sulfonyl]-6-{[(1 -methyl- 1 H-pyrazol-3- yl)carbonyl]amino}-5,16-dioxo-1, 2,3,6,7,8,9,10,11,13a,14,15,16,16a- tetradecahydrocyclopropa[e]pyrrolo[1 ,2-a][1 ,4]diazacyclopentadecine-14a(5H)-Ca; Acid R2a (6.6 mg, 0.052 mmol, 1.3 equiv) is dissolved in DMF (0.5 ml_), then TEA (28muIota_, 0.20 mmol, 5.0 equiv) is added followed by TBTU (15.4 mg, 0.048 mmol, 1.2 equiv). The solution is stirred for 15 mins, after which the amine hydrochloride Ca is added in DMF (0.5 mL) and this solution is stirred at RT for 16 h. Water (2 mL) is added to the solution, and then the organic layer is extracted with EtOAc (3×5 mL) and dried over MgS04. The solvent is evaporated and the residue is purified on prep HPLC (MeCN:H20, 0.1% TFA). The pure fractions are combined, concentrated, frozen and lyophilized to provide compound 1007.FIA M.S.(electrospray) : 820.3 (M+H)+ Retention time (min): 5.7 min1H NMR (400 MHz,DMSO-d6): delta 10.83 (s, 1H) , 8.93 (s, 1H), 7.83 (d, 1H, J = 8.8 Hz), 7.79 (d, 1H, J= 7 Hz), 7.77 (d, 1H, J = 2.1 Hz), 7.08 (d, 1H, J = 9 Hz), 6.60 (d, 1H, J = 2.3 Hz), 6.37 (s, 1H), 5.66-5.58 (m, 1H), 5.62 (S, 1H, J = 6.2 Hz), 5.47-5.44 (m, 1H), 5.07 (dd, 1H, J = 9.5, 9.2 Hz), 4.64-4.54 (m, 1H) 4.52 (d, 1H, J = 11.6 Hz), 4.40 (dd, 1H, J = 9.7, 7.1 Hz), 4.02 (dd, 1H, J = 11.8, 3.5 Hz), 3.89 (s, 3H), 3.88 (s, 3H), 2.66-2.57 (m, 1 H) , 2.51 (s, 3H), 2.43 (s, 3H), 2.38-2.29 (m, 2H), 2.02-1.90 (m, 1H), 1.88-1.77 (m, 1H), 1.58 (dd, 1H, J =8.2, 5.1 Hz), 1.52 (dd, 1H, J =9.3, 5.2 Hz), 1.45-1.35 (m, 12H), 1.34-1.20 (m, 4H), 0.93-0.84 (m, 2H).
According to the analysis of related databases, 25016-20-0, the application of this compound in the production field has become more and more popular.
Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LLINAS-BRUNET, Montse; BORDELEAU , Josee; GODBOUT, Cedrickx; LEBLANC, Melissa; MOREAU, Benoit; O’MEARA, Jeffrey; WO2011/63501; (2011); A1;,
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