Triethylamine → HCID 77146877, compound

Participants

Reaction Steps

30 g of 1-(4-fluorophenyl)-2,5-dimethyl-pyrrole-3-carboxylic acid was reacted with 1 equivalent of 4-(aminomethyl)benzonitrile, in the presence of 1.1 equivalents of oxalyl chloride, 3 equivalents of triethylamine in dichloromethane at room temperature for 3 h. The product was then reacted with hydroxylamine hydrochloride (3 equivalents) in ethanol at 80° C. for 3 h. The target compound (36 g) was obtained as a tan-colored powder following solvent removal by evaporation. Purity assessed by HPLC was 97.8%, and mass was verified by LC/MS/MS (predicted m+1=381.2, obtained m+1=381.2). 1H-NMR (DMSO): δ 1.93 (3H), 2.21 (3H), 4.39-4.40 (2H), 5.76 (2H), 6.42 (1H), 7.26-7.28 (2H), 7.35-7.40 (4H), 7.60-7.62 (2H), 8.22 (1H), 9.56 (1H).

Provenance & Evidence