Reference of 53312-81-5, 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 53312-81-5 as follows.
A solution of Et3N (0.179 mL, 1.29 mmol) in DMF (1.9 mL) was added to 3-fluoro-1-methyl-4-[(3-methyloxetan-3-yl)sulfamoyl]pyrrole-2-carboxylic acidIl25 mg, 0.428 mmol), HATU (204mg, 0.535 mmol), 4-fluoro-3-methylaniline (107 mg, 0.857 mmol) and stirred overnight. The solution was subjected to column chromatography using a gradient from 10 till 100% EtOAc in heptane. The product fractions were combined and concentrated. Compound 94 (78 mg) was obtained as a white powder after drying in vacuo at 50C.J=4.8 Hz, 1 H), 8.56 (d, J=8.8 Hz, 1 H), 13.13 (br. s., 1 H). Compound 170 (531 mg) was synthesized similarly as described for compound 94 using 3-fluoro-1-methyl-4-[[(1R)-2,2,2- trifluoro-1-methyl-ethyl]sulfamoyl]pyrrole-2-carboxylic acid (601.7 mg 1.89 mmol) instead of 3 -fluoro- 1 -methyl-4- [(3 -methyloxetan-3 -yl)sulfamoyl]pyrrole-2-carboxylic acid and 5 -amino-2-fluorobenzonitrile (531 mg, 3.78 mmol) instead of 4-fluoro-3 -methylaniline and the reaction mixture was stirred overnight at 65C. The column fractions were concentrated and the residue was crystallized by dissolving in 100 mL warm methanol upon addition of water. The crystals were filtered off and dried overnight in vacuo at 50C. Method A: Rt: 1.66 mm mlz: 435 (M-H) Exact mass: 436.06.?H NMR (400 MHz, DMSO-d6) oe ppm 1.18 (d, J=6.8 Hz, 3 H), 3.81 (s, 3 H),3.91 – 4.05 (m, 1 H), 7.50 – 7.59 (m, 2 H), 7.96 (ddd, J=9.2, 5.0, 2.8 Hz, 1 H), 8.17 (dd, J=5.8,2.8 Hz, 1 H), 8.62 (d, J=8.8 Hz, 1 H), 10.36 (s, 1 H). Differential scanning calorimetry: From 30 to 300 C at 10C/mm: peak at 190.99 C.
According to the analysis of related databases, 53312-81-5, the application of this compound in the production field has become more and more popular.
Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
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