N-(4-Chloro-2-(hydroxymethyl)-5-(4-(3-(2-methoxyphenyl)-5-methylisoxazole-4-carbonyl)piperazin-1-yl)phenyl)-4-(dimethylamino)benzamide → N-(4-chloro-2-formyl-5-(4-(3-(2-methoxyphenyl)-5-methylisoxazole-4-carbonyl)piperazin-1-yl)phenyl)-4-(dimethylamino)benzamide

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Reaction Steps

A solution of N-(4-chloro-2-(hydroxymethyl)-5-(4-(3-(2-methoxyphenyl)-5-methylisoxazole-4-carbonyl)piperazin-1-yl)phenyl)-4-(dimethylamino)benzamide (60 mg, 0.099 mmol) in DCM (1.2 mL) was added to PCC (300 mg, 0.278 mmol) in an 8-mL vial. The reaction mixture was stirred at RT for 40 min. PCC on basic alumina was removed by filtration. The crude product was purified by flash chromatography (EtOAc/DCM, 20% gradient to 40%, Rf 0.66) to give 11.0 mg of the title compound. 1H-NMR (CDCl3, 400 MHz): δ 12.00 (1H, s), 9.77 (1H, s), 8.58 (1H, s), 7.97 (2H, d, J=9.0 Hz), 7.61-7.56 (2H, m), 7.52-7.45 (1H, m), 7.15-6.99 (2H, m), 6.77 (2H, d, J=9.0 Hz), 3.83 (3H, s), 3.80 (2H, s), 3.26 (2H, s), 3.17 (2H, s), 3.09 (6H, s), 2.59 (3H, s). HPLC/MS (Method H): (ES+) m/z (M+H)+=602; Rt=2.07 min.

Provenance & Evidence