Acetic Acid → HCID 68695975, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of benzooxazol-2-yl-piperidin-4-yl-amine (65.2 mg, 0.3 mmol, 1.0 equiv; free amine of intermediate D) and 5-methyl-2-phenyl-3H-imidazole-4-carbaldehyde (61.5 mg, 0.33 mmol, 1.1 equiv; [CAS RN 68282-50-8] prepared as described in L. A. Reiter J. Org. Chem. 1987, 52, 2714-2726) in ethanol (2 mL) was added acetic acid (54.1 mg, 0.9 mmol, 3.0 equiv) and the reaction mixture heated under microwave irradiation to 100° C. After 10 min, sodium cyano borohydride (24.5 mg, 0.39 mmol, 1.3 equiv) was added and the mixture heated under microwave irradiation to 100° C. for an additional time period of 20 min. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 17.0 mg (15%) of the title compound. MS (ESI): 388.3 [M+H]+.

Provenance & Evidence