Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → methyl 3-phenyl-1-(5-sulfamoylnicotinamido)-1H-pyrrole-2-carboxylate

Participants

Reaction Steps

To a stirred solution of methyl 1-amino-3-phenyl-1H-pyrrole-2-carboxylate (2.00 g, 9.25 mmol) in DMF (20 mL) was added DMAP (3.39 g, 27.7 mmol) and HATU (10.6 g, 27.7 mmol). The reaction mixture was stirred for 15 minutes and a solution of 5-sulfamoylnicotinic acid (3.74 g, 18.5 mmol) dissolved in DMF was added. The reaction mixture was stirred at room temperature for 14 h. The reaction mixture was concentrated under reduced pressure to remove DMF and saturated solution of citric acid was added to the residue until the pH was 3. The solution was extracted with CH2Cl2 and the organic layer was separated, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using CombiFlash (REDISEP®, neutral alumina, 40 g, 13% methanol in CH2Cl2) to afford methyl 3-phenyl-1-(5-sulfamoylnicotinamido)-1H-pyrrole-2-carboxylate (1.20 g, 32.4%). LCMS Condition B-39: retention time 1.79 min, [M−1]=399.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.54 (s, 3H), 6.34 (d, J=3.2 Hz, 1H), 7.32-7.44 (m, 7H), 7.80 (br s, 2H), 8.68 (t, J=2.0 Hz, 1H), 9.20 (d, J=2.0 Hz, 1H), 9.30 (d, J=2.0 Hz, 1H).

Provenance & Evidence