Dimethyl Sulfoxide → HCID 67241715, compound

Participants

Reaction Conditions

Reaction Steps

Combined 2,4-dichlorothiazole (405 mg, 2.63 mmol), 3-oxo-1,4-diazepan-1-ium trifluoroacetate (preparation described in Intermediate XX, 600 mg, 2.63 mmol), potassium phosphate tribasic (1395 mg, 6.57 mmol) and DMSO (22.00 ml) in a round bottomed flask, fitted with water-cooled condenser, balloon and septum. The mixture was heated to 150° C. for 7 hours with stirring. The dark solution was diluted with 100 mL 10% IPA/CHCl3, 40 mL water, mL aq. NaHCO3(sat.). The resulting suspension was extracted with 10% IPA/CHCl3, and the organic layers were combined and washed successively with water and brine. The organic fractions were pooled and concentrated to dryness. The residue was then loaded directly onto silica gel and purified by preparative HPLC Normal phase, eluting with CH2Cl2/MeOH (0-30%). The 3rd peak was collected and concentrated to afford 4-(4-chloro-1,3-thiazol-2-yl)-1,4-diazepan-2-one (179 mg, 0.773 mmol, 29.4% yield) as a brown solid.

Provenance & Evidence