Trifluoroacetic acid → (2S,4R)-4-[4-[6-amino-5-(1,3-benzoxazol-2-yl)-3-pyridyl]pyrazol-1-yl]-N-methyl-pyrrolidine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

Trifluoroacetic acid (5 ml) was added to (2S,4R)-tert-butyl 4-[4-[6-amino-5-(1,3-benzoxazol-2-yl)-3-pyridyl]pyrazol-1-yl]-2-(methylcarbamoyl)pyrrolidine-1-carboxylate (70 mg) under argon. The resulting solution was stirred at 25° C. for 1 hour. The solution was evaporated under reduced pressure. The residue was basified with a solution of ammonia in methanol and the resultant mixture was adsorbed onto silica gel and purified by flash chromatography on silica gel eluting with 1 to 6% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness to afford (2S,4R)-4-[4-[6-amino-5-(1,3-benzoxazol-2-yl)-3-pyridyl]pyrazol-1-yl]-N-methyl-pyrrolidine-2-carboxamide (55 mg) as a solid. NMR Spectrum: (CDCl3) 1.75 (bs, 1H), 2.48-2.58 (m, 1H), 2.68-2.76 (m, 1H), 2.85 (d, 1.5H), 2.87 (d, 1.5H), 3.08 (d, 0.5H), 3.10 (d, 0.5H), 3.43-3.46 (m, 0.5H), 3.46-3.49 (m, 0.5H), 4.11-4.17 (m, 1H), 4.79-4.85 (m, 1H), 6.95 (m, 2H), 7.34-7.42 (m, 2H), 7.58-7.62 (m, 1H), 7.63-7.68 (m, 1H), 7.69 (s, 1H), 7.73-7.78 (m, 2H), 8.36 (d, 1H), 8.38 (d, 1H); Mass spectrum: M+H+ 404.

Provenance & Evidence