Sodium Bicarbonate → HCID 86635320, compound

Participants

Reaction Steps

A mixture of 7-oxo-8-(2-oxoethyl)-7,8-dihydro-1,8-naphthyridine-2-carbonitrile (329 mg, 1.545 mmol) and 1,1-dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)-4-piperidinylcarbamate (for a synthesis see WO2004/058144 Example 99(h)) (539 mg, 1.545 mmol) in chloroform (15 ml) and MeOH (1 ml) was stirred for 2 h before addition of NaBH(OAc)3 (982 mg, 4.635 mmol). The reaction was stirred for 0.5 h before addition of sat. aq NaHCO3 (50 ml). The reaction was then extracted with 20% MeOH in DCM (3×200 ml). The combined organic phases were dried, evaporated and the crude residue purified by chromatography on silica gel using a 0-20% MeOH/DCM gradient to provide the desired compound (620 mg, 73%).

Provenance & Evidence