Diisopropylethylamine → N-[3-(3-pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenyl]-2-(4-trifluoromethyl-phenyl)-acetamide

Participants

Reaction Steps

To a solution of 3-(3-pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenylamine (prepared as described in Example 3) (100 mg, 0.324 mmol) in dichloromethane (8 mL), were added in the following order: (4-trifluoromethyl-phenyl)-acetic acid (132 mg, 0.648 mmol), DIPEA (125 mg, 166 uL, 0.972 mmol) and TBTU (312 mg, 0.972 mmol). The reaction mixture was stirred at room temperature for 3 hours. Then it was poured into a solution of saturated NaHCO3, the phases separated, and the organic phase was washed twice with saturated NaHCO3, and twice with water. The organic solvent was evaporated to dryness and the product was purified by flash chromatography over silica gel using dichloromethane-methanol (98:2) as the eluant system. N-[3-(3-pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenyl]-2-(4-trifluoromethyl-phenyl)-acetamide was obtained as a colorless solid (115 mg, 72%).

Provenance & Evidence