Water → HCID 67353582, compound

Participants

Reaction Steps

To 3-(trifluoromethyl)aniline (0.117 ml), methyl 2-(3-(4-aminophenyl)isoxazole-5-carboxamido)-3-methylbutanoate (300 mg, example 151, step 3) in EtOAc (6 ml), oxalyl chloride was added and stirred at RT for 3 hours. To this water was added and organic layer was collected and dried over Na2SO4 and concentrated to obtain brown solid which was purified by column chromatography (silica gel, EtOAc—CHCl3 to obtain pale brown solid which was crystallized from DCM-Petroleum ether to yield 150 mg (29%) of the title compound as off white solid. MS (ES+): m/z 533 (M+1); 1HNMR (DMSO-d6; 300 MHz): δ 11.24 (s, 1H), 11.14 (s, 1H), 9.25 (d, 1H), 8.35 (dd, 1H), 8.16 (dd, 1H), 8.06 (d, 2H), 7.96 (d, 2H), 7.72 (s, 1H), 7.64 (m, 1H), 7.54 (dd, 1H), 4.31 (m, 1H), 3.68 (s, 3H), 2.23 (m, 1H), 0.97 (d, 6H).

Provenance & Evidence