Dichloromethane → HCID 59627863, compound

Participants

Reaction Steps

A solution of 4-(acetylamino)benzoic acid (33.6 mg, 0.188 mmol) and methylene chloride (0.190 mL) was cooled to 0° C. and treated with thionyl chloride (41 uL, 0.563 mmol) and a drop of DMF. The cold bath was removed, and the reaction progress was checked via piperidine quench and LCMS. The reaction was thoroughly concentrated and dissolved in methylene chloride:THF (1:1, 0.240 mL) and benzyl(2-amino-6-phenylpyridin-3-yl)carbamate (20 mg, 0.0626 mmol) added. After 2 days the reaction was concentrated, taken into DMF and purified via reversed phase HPLC, 20-80% MeCN in water with 0.05% TFA to afford the requisite compound which was taken to the next reaction. MS cal'd 481 (M+H)+, exp 481 (M+H)+.

Provenance & Evidence