Acetyl chloride → HCID 86664056, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 1-[5-[7-cyano-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (327 mg, 0.66 mmol) and hydroxylamine hydrochloride (230 mg, 3.31 mmol) were suspended in pyridine (20 mL) and the mixture stirred at 80° C. for 4 h. The reaction was cooled to rt and acetyl chloride (565 μL, 7.95 mmol) was added then stirred at 80° C. for 9 h. The reaction was diluted with EtOAc (100 mL), washed with dilute HCl (2×100 mL), brine and separated. The organic fraction was dried (Na2SO4) and concentrated under reduced pressure and the oily residue purified by flash column chromatography (40 g GraceResolv silica cartridge—dry loaded), eluting with 50-100% EtOAc/heptane to afford the desired compound (192 mg, 53%) as a white solid. MS: 551.13 [M+H]+.

Provenance & Evidence