Methanesulfonyl chloride → HCID 136163774, compound

Participants

Reaction Steps

To a suspension of (4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)phenyl)methanol (1.35 g, 3.95 mmol) in dichloromethane (70 mL) was added diisopropylethylamine (1.72 mL, 9.89 mmol) and methanesulfonyl chloride (0.767 mL, 9.89 mmol). The reaction mixture was stirred at room temperature for 30 minutes. The mixture was washed with water (50 mL), saturated aqueous sodium bicarbonate solution (50 mL) and water (3×50 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo, yielding the 4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)benzyl methanesulfonate as a light yellow solid (1.7 g, quantitative). M.p.=252-253° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.82 (br.s, 1H), 8.22 (dd, J=4.8, 1.6 Hz, 1H), 7.97 (dd, J=7.6, 1.6 Hz, 1H), 7.6-7.4 (m, 5H), 7.36 (dd, J=8.0, 1.2 Hz, 1H), 7.2-7.1 (m, 2H), 6.92 (dd, J=7.6, 4.4 Hz, 1H), 5.33 (s, 2H), 3.28 (s, 3H); LCMS [M+H]: 420.

Provenance & Evidence