Triethylamine → HCID 18464582, compound

Participants

Reaction Steps

Combine 3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl)ethyl)-3-phenylpyrrolidine hydrochloric acid salt (prepared from (−)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine(R,R)-di-p-anisoyltartaric acid salt) (0.64 g, 1.2 mmol) and dichloromethane (12 mL). Add 2-methoxy-5-(3,5-dimethyl-4H-triazol-4-yl)benzoic acid (0.3 g, 1.2 mmol), 1-hydroxybenzotriazole hydrate (0.17 g, 1.23 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.29 g, 1.5 mmol), and triethylamine (0.34 mL, 2.4 mmol). After 6 days, dilute the reaction mixture with dichloromethane and extract with a saturated aqueous sodium bicarbonate solution and then brine, dry the organic layer over MgSO4, filter, and concentrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 10% methanol/dichloromethane and then 20% methanol/dichloromethane to give a residue. Combine the residue and dichloromethane, extract with water and then brine, dry over Na2SO4, and evaporate in vacuo to give the title compound.

Provenance & Evidence