Acetic Acid → HCID 68698324, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(piperidin-4-ylamino)-benzooxazole-7-carboxylic acid (0.35 g, 1.32 mmol, 1.0 equiv) and 3-ethoxy-4-methoxy-benzaldehyde (0.26 g, 1.45 mmol, 1.1 equiv) in ethanol (2 mL) was added diisopropylethylamine (0.39 mL, 0.43 g, 3.3 mmol, 2.5 equiv) and acetic acid (0.16 g, 2.64 mmol, 2.0 equiv) and the mixture stirred at 50° C. After 1.5 h sodium cyano borohydride (0.21 g, 3.3 mmol, 2.5 equiv) was added and the mixture stirred at 50° C. over night. The solvent was removed under reduced pressure and the crude reaction product dissolved in a mixture (1:1, 50 mL) of ethyl acetate and water adjusted to pH 7. The water phase was extracted two more times with ethyl acetate (2×50 mL), the combined organic phases dried over MgSO4 and the solvent evaporated to yield 0.55 g (99%) of the title compound which was used directly in the following step. MS (ISP): 426.0 [M+H]+.

Provenance & Evidence