Water → HCID 19039945, compound

Participants

Reaction Steps

382 mg (9.54 mmol) of sodium hydride, 60% oil dispersion, were added in one portion to a room temperature solution of 1.76 g (4.54 mmol) of the product of Example 56 in 30 mL of anhydrous DMF. After 20 minutes, a room temperature solution of 1.40 g (6.36 mmol) of 2-chloromethyl-5,6-difluorobenzothiazole in 10 mL of anhydrous DMF was added over 15-20 minutes. After stirring 18 hours at room temperature, the reaction mixture was poured into 500 mL H2O, acidified to pH 1, and extracted two times with 300 mL ethyl acetate. The ethyl acetate extracts were combined, washed three times with 150 mL H2O, one time with 100 mL brine, and dried over Na2SO4. Filtration, concentration and drying gave 3.3 g of a brown oil, which was purified by silica gel chromatography (15% to 25% ethyl acetate in CH2Cl2) to afford 1.52 g of the title product as an off-white solid. 59% yield.

Provenance & Evidence