Trifluoroacetic acid → N-(6-amino-4-methylpyridin-2-yl)-2-(4-cyanophenyl)-4-methyl-1,3-thiazole-5-sulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl [6-({[2-(4-cyanophenyl)4-methyl-1,3-thiazol-5-yl]sulfonyl}amino)-4-methylpyridin-2-yl]carbamate (0.334 g, 0.68 mmol, 1 equiv) in dichloromethane (3 mL) was added trifluoroacetic acid (0.21 mL, 4 equiv). The reaction mixture was stirred at 24° C. for 48 h. The solution was neutralized with saturated aqueous sodium bicarbonate, and the resulting solution was extracted with dichloromethane (3×20 mL). The collected organic was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by high performance flash chromatography (0→1% methanol in dichloromethane) provided the titled product N-(6-Amino-4-methylpyridin-2-yl)-2-(4-cyanophenyl)-4-methyl-1,3-thiazole-5-sulfonamide (0.22 g, 81%). 1H NMR (400 MHz, DMSO-d6), δ: 12.08 (br s, 1H), 8.09 (d, J=8.3 Hz, 2H), 7.95 (d, J=8.3 Hz, 2H), 6.62 (br s, 2H), 6.12 (s, 1H), 5.79 (s, 1H), 2.59 (s, 3H), 2.08 (s, 3H); HRMS (ESI): Calculated for C17H16N5O2S2 m/z 386.0740. Found: 386.0745;. Anal. Calcd for C17H15N5O2S2: C, 52.97; H, 3.92; N, 18.17; Found: C, 52.75; H, 3.76; N, 18.03.

Provenance & Evidence