Trifluoroacetic acid → HCID 15952366, compound

Participants

Reaction Steps

To a solution of tert-butyl 4′-{[3-{[(pyridin-3-ylmethyl)amino]carbonyl}-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-yl]carbonyl}-1,1′-biphenyl-2-carboxylate of Example 64 (0.710 g, 1.186 mmol) in dry dichloromethane (10 mL) was added trifluoroacetic acid (10 mL) and the reaction mixture stirred at room temperature under nitrogen for 1.75 hours. The reaction mixture was then concentrated in vacuo and the resulting solid dissolved in ethyl acetate (50 mL). The organic phase was extracted with 2 M sodium hydroxide (2×50 mL) and the combined aqueous extracts acidified to pH 1 by the addition of concentrated hydrochloric acid. The resulting white suspension was cooled to 4° C. for 1 hour, the solid product filtered, washed with water and then dried in vacuo at 50° C. overnight to afford the title compound (0.345 g, 54%) as a white solid, m.p. 189-191° C.

Provenance & Evidence