Diisopropylethylamine → 6,6-Dimethyl-2-{6-[(6-methylpyridazin-3-yl)oxy]-2,3-dihydro-4h-1,4-benzoxazin-4-yl}-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one

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Reaction Steps

A stirred solution of Example 57 (0.05 g, 0.15 mmol) and 3-chloro-6-methylpyridazine (0.019 g, 0.15 mmol) in DIPEA (0.1 mL, 0.3 mmol) was heated to 180° C. under microwave irradiation in a sealed tube for 4 h, then concentrated in vacuo. Purification by preparative HPLC (Method 7) gave the title compound (0.053 g, 19%) as an off-white solid. δH (CDCl3) 7.98 (1H, d, J 2.4 Hz), 7.34 (1H, d, J 9.0 Hz), 7.08 (1H, d, J 9.0 Hz), 7.00-6.80 (2H, m), 5.45 (1H, s), 4.40-4.30 (2H, m), 4.20-4.10 (2H, m), 2.86 (2H, s), 2.64 (3H, s), 1.38 (6H, s). LCMS (ES+) 424.0 (M+H)+, RT 2.92 minutes (Method 2).

Provenance & Evidence