反应详情

5-[2-(acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride, prepared as in Step I of Example 9 (110 mg; 0.33 mmol; 1 eq.), is dissolved in a mixture of DCM/DMF (1/1, 10 ml). 4-Amino-1-methylpiperidine (188 mg; 1.65 mmol; 5 eq.) and DIEA (0.17 ml; 0.98 mmol; 3 eq.) are added. After 3 hours, the solvents are evaporated. The crude product is dissolved in DCM and washed with NH4C1 saturated solution, water and dried over MgSO4. After evaporation of the solvents, crude material is dissolved in DCM (3 ml) and title compound precipitated with Et2O affording after filtration, compound (4) as a white powder (120 mg; 90%). 1H NMR (DMSO-d6) δ 1.25 (m, 2H), 1.55 (m, 2H), 1.80 (m, 2H), 2.05 (m, 2H), 2.25 (s, 6H), 2.40 (s, 3H), 3.05 (m, 1H), 6.95 (d, J=3 Hz, 1H), 7.52 (d, J=3 Hz, 1H), 12.23 (m, 1H). M− (ESI): 413.30; M+ (ESI): 415.30. HPLC, Rt: 2.08 min (purity: 99.33%).

1. customthe solvents are evaporated
2. dissolutionThe crude product is dissolved in DCM
3. washwashed with NH4C1 saturated solution, water
4. dry with materialdried over MgSO4
5. customAfter evaporation of the solvents, crude material
6. dissolutionis dissolved in DCM (3 ml)
7. customtitle compound precipitated with Et2O affording
8. filtrationafter filtration, compound (4) as a white powder (120 mg; 90%)