Dimethyl Sulfoxide → HCID 178516777, compound

Participants

Reaction Steps

DMSO (170 μL, 2.4 mmol) was added dropwise to a solution of oxalyl chloride (105 μL, 1.2 mmol) in dry CH2Cl2 (10 mL) cooled in a dry ice/acetone bath. The reaction mixture was stirred with cooling for 30 min. A solution of 1-(trans-4-{[(5-nitro-2-{[2-(trifluoromethoxy)benzyl]amino}pyrimidin-4-yl)amino]methyl}cyclohexyl)azetidin-3-ol (200 mg, 0.4 mmol) in dry CH2Cl2 was added dropwise and the reaction was allowed to stir for 2 h. Et3N (501 μL, 3.6 mmol) was then added and the reaction mixture was stirred for 16 h and allowed to slowly warm to room temperature. The mixture was diluted with CH2Cl2 and poured into saturated aqueous Na2SO4. The aqueous phase was separated and extracted with CH2Cl2 (×2). The combined organic phase was dried over Na2SO4, decanted and concentrated. The crude product was purified by flash chromatography on a 120 g SiO2 column, eluting with 90:9:1 CH2Cl2:MeOH:NH4OH as an eluent to afford 147 mg (74%) of the title compound, m/z 495.6 [M+1]+.

Provenance & Evidence