1-Hydroxybenzotriazole → HCID 74440995, compound

Participants

Reaction Steps

To a suspension of 4-(3-(cyclopropylamino)-2-(p-tolyl)-3-oxoprop-1-en-1-yl)benzoic acid (0.1 g, 0.3 mmol) in DMF (3 mL), benzotriazol-1-yloxy-tris(dimethyl amino)phosphonium hexafluorophosphate (BOP reagent, 0.23 g, 0.55 mmol), HOBt (0.04 g, 0.3 mmol), hydroxylamine hydrochloride (0.03 g, 0.35 mmol), were added followed by DIPEA (0.16 mL, 0.9 mmol). The reaction mixture was stirred for 1 hour, after which the mixture was added to cold water (100 mL) and kept it for 1 hour at 0° C. the white solid formed. The obtained solid was filtered and washed with water (50 mL), dried under vacuum to afford the title compound as white solid (0.080 g, 77% yield). 1H NMR (DMSO-d6) δ (ppm): 0.46-0.51 (2H, m, —CH2), 0.58-0.60 (2H, m, —CH2), 2.29 (3H, s, CH3), 2.69-2.70 (1H, m, —CH), 6.81 (4H, m, Ar—H), 6.97-7.03 (3H, m, Ar—H), 7.36-7.38 (I+1H, d, Ar—H and ═CH), 7.70 (1H, d, NH), 8.99 (1H, s, OH), 11.10 (1H, s, NH), MS m/z: 337.1 (M++1).

Provenance & Evidence