Dimethylformamide → HCID 58919238, compound

Participants

Reaction Steps

A solution of tert-butyl 4-(3-(azidocarbonyl)-2,4-difluorobenzyl)piperazine-1-carboxylate (2.52 g, nominally 5.4 mmol, 1.0 equiv) and 6-methylpyridin-3-amine (389 mg, 3.6 mmol, 0.66 equiv) in 7 mL of DMF was stirred at room temperature over 72 h, after which, the reaction mixture was diluted with EtOAc and washed repeatedly with water. After the EtOAc layer was washed with aq. satd. NaHCO3 and brine, it was dried over sodium sulfate, filtered and concentrated in vacuo. Reverse phase chromatography provided tert-butyl 4-(2,4-difluoro-3-(3-(6-methylpyridin-3-yl)ureido)benzyl)piperazine-1-carboxylate (800 mg, 32% over 4 steps). LCMS m/z (APCI)=462.2 (M+H).

Provenance & Evidence