Hydrochloric Acid → HCID 68997028, compound

Participants

Reaction Steps

To a solution of 1-[2-(4-amino-1-piperidinyl)ethyl]-7-fluoro-2-oxo-1,2-dihydro-4-quinolinecarbonitrile hydrochloride (0.062 g, 0.16 mmol) and 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carboxaldehyde (for a synthesis see WO2003087098, Example 31(e))(0.028 g, 0.16 mmol) in 1:1 chloroform/methanol (6 ml) was added sodium acetate (00.10 g, 12 mmol), acetic acid (0.5 ml) and 3A sieves and the mixture stirred for 1 h. Polymer supported cyanoborohydride (0.10 g) was added and the mixture stirred for 18 h, then filtered and the solid washed with dichloromethane. The organics were washed with sodium carbonate solution, dried and concentrated. Chromatography over silica (10 g SPE gradient elution with dichloromethane/methanol 0-15%) provided the product which was dissolved in dichloromethane and treated with 4M HCl in 1,4-dioxane. The precipitate was isolated and washed with ether then dried to provide the title compound (0.048 g, 55%).

Provenance & Evidence