3-(Chloromethyl)pyridazine → 7,7-Dimethyl-2-{6-[(6-methylpyridazin-3-yl)amino]-2,3-dihydro-4h-1,4-benzoxazin-4-yl}-5,6,7,8-tetrahydro-4h-[1,3]thiazolo[5,4-c]azepin-4-one acetate salt

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Reaction Steps

A mixture of Example 69 (100 mg, 0.29 mmol), chloromethylpyridazine (20 mg, 0.29 mmol), sodium tert-butoxide (80 mg, 0.8 mmol) and dichloro(1,1′-bis(di-tert-butylphosphino)ferrocene)palladium (10 mg, catalytic) in toluene (5 mL) was heated to 120° C. under microwave irradiation for 2 h. It was cooled to r.t., concentrated in vacuo and purified by prep HPLC to give the title compound (14 mg, 9%) as an off-white solid. δH (CD3OD/CDCl3) 1.11 (6H, s), 2.02 (3H, s), 2.54 (3H, s), 2.85 (2H, s), 3.12 (2H, s), 4.09-4.17 (2H, m), 4.29-4.35 (2H, m), 6.94 (1H, d, J 8.9 Hz), 7.10-7.30 (3H, m), 7.99 (1H, s). LCMS (ES+) 437 (M+H)+.

Provenance & Evidence