Triethylamine → HCID 69099565, compound

Participants

Reaction Steps

A solution of ethyl 2-[4-(2-{(5-aminopyridin-2-yl)[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (65 mg; 0.13 mmol) in 3 ml of dichloromethane was treated with Et3N (0.019 ml; 0.14 mmol) and methanesulfonyl chloride (0.011 ml; 0.14 mmol). After 30 minutes, additional amounts of Et3N (0.019 ml) and methanesulfonyl chloride (0.011 ml) were added and stirred for another 30 minutes. The reaction mixture was concentrated and the residue partitioned between ethyl acetate and 0.5N HCl. The organic phase was washed with 0.5N HCl and brine, dried over sodium sulfate and concentrated. Purification by radial chromatography using an ethyl acetate-hexane gradient (10–70%) provided two main products: ethyl 2-methyl-2-[4-(2-{{5-[(methylsulfonyl)amino]pyridin-2-yl}[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]propanoate (10 mg; 13% yield; MS: m/z 580 (M+1)) and ethyl 2-[4-(2-{{5-[bis(methylsulfonyl)amino]pyridin-2-yl}[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (39 mg; 46% yield; MS: m/z 658 (M+1)). (Both of these products can be hydrolyzed to the title compound).

Provenance & Evidence