Trifluoroacetic acid → HCID 10120551, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 58 mg (0.1 mmol) of N-({3-[(2,5-dimethoxyphenyl) hydroxymethyl](imidazolo[1,2-a]pyridin-2-yl)}methyl)(2-chloro-3,4-dimethoxyphenyl)-N-(3-methylbutyl)carboxamide in 5 mL dichloromethane is treated with 116 mg (1.0 mmol) triethylsilane and 114 mg (1.0 mmol) trifluoroacetic acid. The solution is heated in a sealed tube at 60° C. for 18 hr and diluted with 15 mL sat. NaHCO3 and extracted with 3×10 mL dichloromethane. The combined organics are washed with 10 mL water and 10 mL brine. The resulting organic layer is dried over anhydrous MgSO4 and the solvent removed in vacuo to give the crude material. The residue is prep-plate chromatographed (9% MeOH/CH2Cl2/0.5% NH4OH) to afford 33 mg (58%) N-({3-[(2,5-dimethoxyphenyl)methyl](imidazolo[1,2-a]pyridin-2-yl)}methyl)(2-chloro-3,4-dimethoxyphenyl)-N-(3-methylbutyl)carboxamide. Mass Spec m/z (M++1) 567.

Provenance & Evidence