Sodium borohydride → HCID 11720253, compound

Participants

Reaction Steps

4-oxo-piperidine-1-carboxylic acid (4-{[2-(2-methyl-2H-indazol-6-ylcarbamoyl)-phenylamino]-methyl}-pyridin-2-yl)-amide (50 mg, 0.1 mmol) in absolute EtOH, at 4° C. was treated with sodium borohydride (4 mg, 0.1 mmol). The reaction was warmed to rt and stirred for 1 hour before the reaction was partitioned between EtOAc and water. The organic phase was washed with brine, dried, filtered and concentrated in vacuo to give 4-hydroxy-piperidine-1-carboxylic acid (4-{[2-(2-methyl-2H-indazol-6-ylcarbamoyl)-phenylamino]-methyl}-pyridin-2-yl)-amide (39 mg, 78%) as a solid; 1H-NMR (300 MHz, d6-DMSO) 10.14 (1H, s), 9.07 (1H, s), 8.26 (1H, s), 8.14 (1H, d), 8.10 (1H, s), 7.94 (1H, t), 7.79 (1H, s), 7.71-7.73 (1H, m), 7.64 (1H, d), 7.30-7.33 (1H, m), 7.23-7.28 (1H, m), 6.92-6.94 (1H, m), 6.66 (1H, t), 6.54 (1H, d), 4.68 (1H, d), 4.43 (2H, d), 4.13 (3H, s), 3.79-3.84 (2H, m), 3.60-3.67 (1H, m), 3.00-3.08 (2H, m), 1.70-1.73 (2H, m), 1.23-1.35 (2H, m); m/z (ES+) 500 [M+H]+.

Provenance & Evidence