Ammonia → HCID 67388808, compound

Participants

Reaction Steps

Aluminium(III) lithium hydride (0.251 ml, 1M in THF) was added dropwise to methyl 2-[2-amino-5-[1-(1-tert-butoxycarbonyl-4-piperidyl)pyrazol-4-yl]-3-pyridyl]-1,3-benzoxazole-7-carboxylate (130 mg) dissolved in THF (5 ml). 7N Methanolic ammonia (15 ml) was added to the mixture and the solution was adsorbed on silica gel and the solvent was evaporated. The crude product was purified by flash chromatography on silica gel eluting with 1 to 4% methanol in dichloromethane. The solvent was evaporated to dryness to afford tert-butyl 4-[4-[6-amino-5-[7-(hydroxymethyl)-1,3-benzoxazol-2-yl]-3-pyridyl]pyrazol-1-yl]piperidine-1-carboxylate (56.0 mg) as a clear yellow solid. NMR Spectrum: (CDCl3): 1.49 (s, 9H), 1.96 (dd, 1H), 2.00 (dd, 1H), 2.13-2.24 (m, 2H), 2.84-3.01 (m, 2H), 4.17-4.44 (m, 3H), 5.09 (s, 2H), 6.98 (bs, 2H), 7.37 (dd, 1H), 7.43 (s, 1H), 7.66 (s, 1H), 7.67 (d, 1H), 7.76 (s, 1H), 8.28 (d, 1H), 8.33 (d, 1H); Mass spectrum: M+H+ 491;

Provenance & Evidence