Triethylamine → HCID 57786389, compound

Participants

Reaction Steps

To a solution of 1-[9-chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]propan-1-ol (150 mg, 0.365 mmol), (methylsulfonyl)acetic acid (81.6 mg, 0.59 mmol), triethylamine (0.11 mL, 0.789 mmol) and 4-dimethylaminopyridine (48.0 mg, 0.39 mmol) in tetrahydrofuran (5.0 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (136 mg, 0.709 mmol) at room temperature. The mixture was stirred at room temperature for 3 days. (Methylsulfonyl)acetic acid (82.0 mg, 0.59 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (140 mg, 0.73 mmol), triethylamine (0.11 mL, 0.789 mmol) and N,N-dimethylformamide (10 mL) were added to the reaction mixture at room temperature. The mixture was stirred at room temperature for 24 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on NH-silica gel eluting with a 40-70% ethyl acetate/n-hexane gradient mixture and recrystallization from 2-propanol/diisopropyl ether to give the title compound (68.9 mg, 0.13 mmol, 36%) as colorless crystals.

Provenance & Evidence