2-Methoxyethyl chloroformate → 2-Methoxyethyl 4-[4-(6-amino-5-oxazolo[4,5-b]pyridin-2-yl-3-pyridyl)pyrazol-1-yl]piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

2-methoxyethyl chloroformate (0.035 ml) at 25° C. was added over a period of 5 minutes under argon to a stirred mixture of 3-oxazolo[4,5-b]pyridin-2-yl-5-[1-(4-piperidyl)pyrazol-4-yl]pyridin-2-amine (90 mg) and pyridine (5 ml). The resulting suspension was stirred at 25° C. for 2 hours. The solvent was evaporated. A solution of ammonia in methanol 7N (1 ml) was added and the mixture was adsorbed on silica gel. The crude product was purified by flash chromatography on silica gel eluting with 1 to 5% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness to afford 2-methoxyethyl 4-[4-(6-amino-5-oxazolo[4,5-b]pyridin-2-yl-3-pyridyl)pyrazol-1-yl]piperidine-1-carboxylate (75 mg) as a solid. NMR Spectrum: (CDCl3): 1.95-2.07 (m, 2H), 2.17-2.26 (m, 2H), 3.01 (bs, 2H), 3.40 (s, 3H), 3.63 (t, 2H), 4.28 (bs, 2H), 4.29-4.44 (m, 3H), 7.02 (bs, 2H), 7.35 (dd, 1H), 7.69 (s, 1H), 7.79 (s, 1H), 7.90 (dd, 1H), 8.41 (d, 1H), 8.42 (d, 1H), 8.59 (dd, 1H); Mass spectrum: M+H+ 464.

Provenance & Evidence