Triethylamine → HCID 68997033, compound

Participants

Reaction Steps

A mixture of 4-[2-(4-amino-1-piperidinyl)ethyl]-6-(methyloxy)-1,2,4-benzotriazin-3(4H)-one dihydrochloride (42 mg, 0.112 mmol) in chloroform (2 ml) and MeOH (0.1 ml) was treated with triethylamine (50 μl, 0.358 mmol) and stirred for 0.25 h before addition of 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carboxaldehyde (for a synthesis see WO2004058144, Example 2(c) or WO03/087098, Example 19(d)) (18 mg, 0.112 mmol). The reaction was stirred for 0.5 h before addition of NaBH(OAc)3 (71 mg, 0.336 mmol). The reaction was stirred for 1 h before addition of sat. aq NaHCO3 (10 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 free base of the title compound (26 mg, 51%).

Provenance & Evidence