Water → HCID 19039964, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2.36 (7.21 mmole) of the product of Example 102 in 25 mL DMF at 0° C. was added 332 mg (8.29 mmole) 60% sodium hydride. The mixture was stirred at 0° C. then a solution of 2.06 g (9.37 mmole) 2-(chloromethyl)-5,6-difluorobenzothiazole in 15 mL DMF was added dropwise. The mixture was slowly warmed to room temperature and stirred for 18 hours. The mixture was poured into water and then extracted with ethyl acetate. The ethyl acetate extract was washed successively with 1N KOH, water and brine and then dried (MgSO4) and concentrated to give an oil. Flash chromatography on silica gel eluting with 50% ethyl acetate in hexanes gave 2.3 g (62%) of the title product as a solid. NMR (CDCl3): δ1.45 (d, 6H); 2.90 (m, 3H); 3.69 (s, 3H); 5.39 (s, 2H). MS (Cl, NH3) m/e: 528 (M+ +18), 511 (M+ +1,100).

Provenance & Evidence