反应详情

温度

0 °C

To a solution of 4-(6-chlorobenzo[d]thiazol-2-ylamino)-N′-(3-chloropyrazin-2-yl)benzohydrazide (63B) (6.17 g, 14.31 mmol) in a mixed solvent of CCl4 (60 mL), THF (80 mL) and CH2Cl2 (120 mL) cooled to 0° C. under argon was added DIPEA (18.49 g, 143 mmol), followed by dropwise addition of triethylphosphine (8.45 g, 71.5 mmol). After addition, the reaction mixture was stirred at 0° C. for 1 h, and then quenched by addition of water (100 mL). The precipitate was isolated by filtration and air dried to yield the first crop of the title compound as a dark brown solid (3.92 g). The filtrate was extracted with ethyl acetate (2×). The combined organics were washed with water (1×100 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The obtained residue was triturated with CH3OH/CH2Cl2 (35 mL/5 mL) to yield the second crop of the title compound (0.95 g) (total 4.87 g, 82% yield). HPLC/MS (Method C): retention time=2.61 min, [M+H]+=413.3. 1H NMR (500 MHz, DMSO-d6): δ 10.98 (s, 1H), 8.68 (d, J=4.95 Hz, 1H), 8.05 (d, J=8.25 Hz, 2H), 7.98 (s, 1H), 7.96 (d, J=825 Hz, 2H), 7.77 (d, J=4.95 Hz, 1H), 7.63 (d, J=8.25 Hz, 1H), 7.37 (d, J=8.80 Hz, 1H).

1. additionAfter addition
2. customquenched by addition of water (100 mL)
3. customThe precipitate was isolated by filtration and air
4. customdried