Trifluoroacetic acid → HCID 71075277, compound

Participants

Reaction Steps

To a solution of tert-butyl {3-(acetylamino)-5-[2-(3-oxo-1,4-diazepan-1-yl)-1,3-thiazol-5-yl]phenyl}[4-(trifluoromethyl)pyrimidin-2-yl]carbamate (79 mg, 0.134 mmol) in dichloromethane (1 mL) at room temperatrue, under nitrogen, was added trifluoroacetic acid (1 mL, 13 mmol). The mixture was stirred at room temperature for 1 h and concentrated to dryness. The residue was partitioned between ethyl acetate and 5% aqueous sodium bicarbonate. The solid product precipitated in the two phases. The organic layer was concentrated to dryness and the residue was transferred into the aqueous with a small amount of EtOH. The resulting aqueous suspension was filtered, the solids collected, and washed with water, a small amount of ethanol, then hexane, and dried to afford 48 mg (0.098 mmol, 73% yield) of N-(3-[2-(3-oxo-1,4-diazepan-1-yl)-1,3-thiazol-5-yl]-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)acetamide as an off-white solid. MS APCI: [M+H]+ m/z 492.1. 1H NMR (400 MHz, d6-dmso): δ 10.25 (s, 1H); 9.98 (s, 1H); 8.82 (d, J=4.9 Hz, 1H); 7.75 (m, 2H); 7.61 (br t, J=5.0 Hz, 1H); 7.43-7.37 (m, 2H); 7.28 (d, J=4.9 Hz, 1H); 4.19 (s, 2H); 3.81 (m, 2H); 3.24 (m, 2H); 2.05 (s, 3H); 1.80 (m, 2H). rhSyk=+++.

Provenance & Evidence