Dimethylformamide → HCID 86664055, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 1-[5-[7-bromo-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (600 mg, 0.658 mmol), zinc cyanide (96 mg, 0.822 mmol) and Pd(PPh3)4 (76 mg, 0.066 mmol) were suspended in DMF (10 mL) and degassed/purged (×3) with Ar. The reaction mixture was then heated at 100° C. under microwave irradiation for 40 mins, cooled to rt, diluted with EtOAc (50 mL), washed with water, brine and separated. The organic fraction was dried (Na2SO4) and concentrated under reduced pressure and the resulting solid purified by flash column chromatography (40 g GraceResolv silica cartridge—dry loaded), eluting with 0-10% MeOH/CH2Cl2. The resulting residue was washed with MeOH to afford desired compound (327 mg, ˜100%) as an off-white solid. MS: 494.14 [M+H]+.

Provenance & Evidence