Dimethylamine → HCID 15952369, compound

Participants

Reaction Steps

To a solution of 4′-{[3-{[(pyridin-3-ylmethyl)amino]carbonyl}-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-yl]carbonyl}-1,1′-biphenyl-2-carboxylic acid of Example 65 (92 mg, 0.17 mmol) in 1-methyl-2-pyrrolidinone (4.5 mL) was added a 2.0 M solution of dimethylamine in tetrahydrofuran (0.42 mL, 0.848 mmol) followed by O-(7-azabenzotriazol-1-yl)-N,N,N′,N′,tetramethyluronium hexafluorophosphate (71 mg, 0.187 mmol) and the reaction mixture stirred at room temperature under nitrogen for 2 hours. The reaction mixture was then partitioned between ethyl acetate (50 mL) and 2 M sodium hydroxide (50 mL). The organic phase was separated, washed with 2 M sodium hydroxide (50 mL), water (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford a white foam. Purification by flash chromatography using a solvent gradient of 1 to 7% methanol in dichloromethane gave a colorless glass that was crystallized from ethyl acetate/hexane to afford the title compound 0.082 g, 85%) as a white solid, m.p. 206-207° C.

Provenance & Evidence