Dimethylformamide → HCID 59252802, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-(1H-indol-5-yl)-2,2-dimethyl-3-phenyl-N-(thiazol-2-yl)propanamide (Example 101, 25 mg, 0.067 mmol) in anhydrous acetonitrile (1 mL) was added chlorosulfonyl isocyanate (0.007 mL, 0.074 mmol) at 0° C. under argon. The reaction mixture was stirred at 0° C. for 30 min before anhydrous DMF (0.006 mL, 0.074 mmol) was added. After the reaction mixture was stirred at 0° C. for 30 min and at rt for 1 hr, it was concentrated, mixed with saturated aqueous sodium bicarbonate solution (5 mL), and extracted with dichloromethane (10 mL). The dichloromethane extract was dried (Na2SO4) and concentrated. Silica gel flash chromatography gave 3-(3-cyano-1H-indol-5-yl)-2,2-dimethyl-3-phenyl-N-(thiazol-2-yl)propanamide (Example 108, 11 mg, 0.027 mmol, 41% yield) as a white solid. MS found: (M+H)+=401. 1H-NMR (400 MHz, Acetone-d6): δ ppm 11.15 (1 H, s) 10.48 (1H, s) 8.06 (1H, d, J=2.40 Hz) 7.78 (1H, s) 7.46-7.53 (3H, m) 7.39 (1 H, d, J=8.65 Hz) 7.35 (1H, d, J=3.56 Hz) 7.28 (2H, t, J=7.38 Hz) 7.18 (1H, t, J=7.38 Hz) 7.04 (1H, d, J=3.56 Hz) 5.04 (1H, s) 1.51 (6H, d, J=2.54 Hz).

Provenance & Evidence