反应详情

HATU (0.14 g, 0.37 mmol) and racemic-(trans)-2-{4-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxylic acid (I-2m) (0.12 g, 0.28 mmol) in DMF (10 mL) were stirred at RT for 45 min, then (4-pyridinylmethyl)amine (0.36 g, 3.33 mmol) was added. The solution was stirred at RT for 16 h, then saturated NaHCO3 solution (50 mL) and ethyl acetate (50 mL) were added. The organic layer was separated, washed with saturated NaHCO3 solution (50 mL), water (50 mL), brine (50 mL), dried over MgSO4, filtered and concentrated. The crude material was partially dissolved in dichloromethane (10 mL) and diethyl ether was added (10 mL). The white solid was filtered, washed with diethyl ether, and dried to give the title compound as a white powder (0.094 g, 64%). 1H NMR (400 MHz, CDCl3) δ 8.56 (d, J=5.1 Hz, 2H), 7.97 (d, J=8.4 Hz, 2H), 7.65 (d, J=8.2 Hz, 2H), 7.20 (d, J=4.7 Hz, 2H), 6.96 (d, J=8.1 Hz, 2H), 6.60 (d, J=8.4 Hz, 2H), 5.99 (t, J=5.7 Hz, 1H), 4.49 (t, J=5.9 Hz, 2H), 4.45 (s, 2H), 4.02 (bs, 1H), 2.49 (s, 3H), 2.49-2.45 (m, 1H), 1.63-1.53 (m, 2H), 1.25-1.21 (m, 1H). ES-MS m/z 523.2 (MH+).

1. customThe organic layer was separated
2. washwashed with saturated NaHCO3 solution (50 mL), water (50 mL), brine (50 mL)
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated
6. dissolutionThe crude material was partially dissolved in dichloromethane (10 mL)
7. additiondiethyl ether was added (10 mL)
8. filtrationThe white solid was filtered
9. washwashed with diethyl ether
10. customdried