Acetic Acid → HCID 45485761, compound

Participants

Reaction Steps

Sodium cyanoborohydride (8.0 mg, 0.13 mmol) was added in portions to a stirred mixture of 5-(5-formyl-1-benzothien-2-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile 227 (40 mg, 0.098 mmol), piperidine (10 mg, 0.12 mmol) and acetic acid (7.0 mg, 0.12 mmol) in EtOH (3.0 mL). The resulting mixture was stirred at r.t. overnight and diluted with CH2Cl2 (30 mL). Silica gel and potassium bicarbonate (20 mg) were added and the mixture was concentrated to give a solid residue which was purified by silica gel flash column chromatography (eluting with 3% MeOH in CH2Cl2) to give 26 mg (57%) of 4-[(4-methyl-1H-indol-5-yl)amino]-5-[5-(piperidin-1-ylmethyl)-1-benzothien-2-yl]nicotinonitrile 228 as an off-white solid (MS: 478.3 (M+H); melting range: 180-182° C.; HPLC retention time: 7.1 min.), and 7 mg (18%) of 5-[5-(hydroxymethyl)-1-benzothien-2-yl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile 229 as an off-white solid (MS: 411.3 (M+H); melting range: 174-175° C., HPLC retention time: 8.6 min.(a)).

Provenance & Evidence