4-Methylmorpholine → HCID 18412459, compound

Participants

Reaction Steps

308 mg (1.0 mMol) of 1-methyl-2-[(4-cyanophenyl)oxymethyl]-5-carboxy-imidazo[4.5-b]pyridine were suspended in 5 ml of dimethylformamide and mixed with 303 mg (3.0 mMol) of N-methyl-morpholine and 321 mg (1.0 mMol) of O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyl-uronium tetrafluoroborate. After 10 minutes at room temperature a solution of 215 mg (1.2 mMol) of methyl N-(2-pyridyl)-3-amino-propionate in 2 ml of dimethylformamide was added, whereupon a clear solution was obtained. After 12 hours at room temperature the reaction solution was stirred into ice-water. After extracting 3 times with ethyl acetate the combined organic extracts were washed with a saline solution, dried over sodium sulphate and evaporated down. The residue obtained was chromatographed on silica gel with dichloromethane/ethanol (90:1 to 25:1). Yield: 165 mg of white powder (35% of theory), C25H12N6O4 (407.50) Melting point: 139-140° C.

Provenance & Evidence