4-Methylmorpholine → HCID 86591639, compound

Participants

Reaction Steps

A solution of N1-(4-methoxyquinolin-2-yl)propane-1,3-diamine dihydrochloride (193 mg, 0.63 mmol) [from example 1d], 1-benzyl4,6-dichloro-1H-indole-2-carboxylic acid (203 mg, 0.63 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (182 mg, 0.95 mmol), 1-hydroxybenzotriazole hydrate (94 mg, 0.70 mmol), and N-methylmorpholine (244 μl, 2.22 mmol) in anhydrous N,N-dimethylformamide (5 ml) was stirred for 2 days. The resulting slurry was taken into water (50 ml) and 10% sodium hydroxide solution (10 ml). Extracted into ethyl acetate. The extracts were dried (sodium sulfate) and evaporated to an oil. Column chromatography on silica (2:1 ethyl acetate/hexanes) gave 1-benzyl-4,6-dichloro-1H-indole-2-carboxylic acid [3-(4-methoxy-quinolin-2-ylamino)-propyl]-amide (269 mg, 80%) as a white solid. [M+H]+ 533.

Provenance & Evidence