Triethylamine → HCID 9851664, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 90 mg (0.25 mmol) ({3-[(5-bromo-2-hydroxyphenyl)methyl](imidazolo[1,2-a]pyridin-2-yl)}methyl)(3-methylbutyl)amine in 4 mL dichloromethane at 0° C. is treated with triethylamine 50 mg (0.50 mmol) and then 2-chloro-3,4-dimethoxybenzoylchloride 110 mg (0.50 mmol). The solution is stirred overnight and the volatiles removed by rotary evaporation. The residue is dissolved in 4 mL methanol and treated with 2 mL 1M sodium hydroxide. The solution is heated to 45° C. for 1 hr and the volatiles removed by rotary evaporation. The mixture is acidified with 1M hydrochloric acid, extracted with 3×5 mL ethyl acetate and the combined extracts washed with 5 mL brine. The combined extract is dried over anhydrous MgSO4 and the solvent removed in vacuo to yield 120 mg (80%) N-({3-[(5-bromo-2-hydroxyphenyl)methyl](imidazolo[1,2-a]pyridin-2-yl)}methyl)(2-chloro-3,4-dimethoxyphenyl)-N-(3-methylbutyl)carboxamide. Mass Spec m/z (M++1) 602.

Provenance & Evidence