Methanol → HCID 86647577, compound

Participants

Reaction Steps

Hydroxylamine hydrochloride (0.55 g, 8 mmol) in methanol (2 mL) was mixed with KOH (0.45 g, 8 mmol) in methanol (2 mL) at 0° C. and sonicated for 2 minutes and the white precipitate formed was filtered. The filtrate was added to methyl 3-((3-(4-(3-(cyclopropylamino)-2-(4-fluorophenyl)-3-oxoprop-1-enyl)phenyl)acrylamido)methyl)benzoate (0.22 g, 0.44 mmol) in DCM (1.5 mL) and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was diluted with water (200 mL) and extracted with ethyl acetate (1×200 mL). The ethyl acetate layer was washed with water (100 mL), dried over anhydrous Na2SO4 and concentrated to obtain a crude compound followed by trituration with DCM (15 mL). The obtained solid was filtered and washed with DCM (5 mL) to afford the title compound (0.044 g, 20% yield). 1H NMR (DMSO-d6) δ (ppm): 0.51 (2H, m, —CH2), 0.62-0.65 (2H, m, —CH2), 2.73-2.75 (1H, m, —CH), 4.37-4.38 (2H, d, —CH2), 6.62-6.66 (1H, d, ═CH), 7.00-7.02 (2H, d, Ar—H), 7.15-7.19 (3H, m, Ar—H), 7.21-7.27 (3H, d, Ar—H and ═CH), 7.35 (2H, d, Ar—H), 7.38-7.40 (2H, m, Ar—H and NH), 7.69-7.71 (2H, d, Ar—H), 7.83-7.84 (1H, d, ═CH), 8.63 (1H, t, NH). MS m/z: 500.1 (M++1).

Provenance & Evidence