反应详情

A suspension of 1-(6-(1-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)azetidin-3-ol (Reference Example 2, 0.143 g, 0.50 mmol), N,N-diisopropylethylamine (0.105 mL, 0.60 mmol), and 1-(4-nitrophenylsulfonyl)-1H-1,2,4-triazole (0.178 g, 0.70 mmol) in dichloromethane (5.0 mL) was stirred a few hours and then triethylamine (0.14 mL, 1.0 mmol) was added. After the mixture had been stirred overnight additional 1-(4-nitrophenylsulfonyl)-1H-1,2,4-triazole (0.076 g, 0.30 mmol) was added. The mixture was stirred another day and then placed directly onto a column of silica and purified chromatographically (100% CH2Cl2 to 80:20 CH2Cl2/ethyl acetate) to give 1-(6-(1-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)azetidin-3-yl 4-nitrobenzenesulfonate. 1H NMR (300 MHz, CD3OD) δ ppm 3.91 (s, 3H), 4.20-4.25 (m, 2H), 4.46-4.52 (m, 2H), 5.41-5.50 (m, 1H), 7.46 (d, J=8 Hz, 1H), 7.52 (dd, J=1, 8 Hz, 1H), 7.79 (s, 1H), 7.87 (s, 1H), 7.92 (s, 1H) 8.24 (d, J=9 Hz, 2H), 8.51 (d, J=9 Hz, 2H); MS (ESI) m/z 472 (M+H)+.

1. additionwas added
2. stirringThe mixture was stirred another day
3. custompurified chromatographically (100% CH2Cl2 to 80:20 CH2Cl2/ethyl acetate)