Acetic Acid → HCID 470669, compound

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The 2-chloro-5,11-dihydro-11-ethyl-8-formyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.50 g, 0.16 mmol) was dissolved/suspended in methanol (2 mL) and treated with sodium cyanoborohydride (0.030 g, 0.47 mmol) followed by aniline (0.043 mL, 4.7 mmol). The mixture was stirred for 5 minutes then acetic acid (0.020 mL, 0.35 mmol) was added. After an additional 3 hours at room temperature the mixture was made alkaline with 15% sodium hydroxide and the white suspension was extracted with dichloromethane (3×10 mL). The combined organics were washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by column chromatography then chromatotron (hexane to 1:1 hexanes/ethyl acetate gradient) to give the title compound (0.031 g, 50%), m.p. 79°-80° C.

Provenance & Evidence