Sodium hydride → 2-(4-Chloro-phenyl)-5-[3-methoxy-4-(3-methyl-3H-imidazol-4-ylmethoxy)-phenyl]-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one

Participants

Reaction Steps

Treat a solution of (3-methyl-3H-imidazol-4-yl)-methanol (60.0 mg, 0.54 mmol) in CH2Cl2 with oxalyl chloride (0.15 g, 1.2 mmol) and 2 drops of DMF. Stir at room temperature for 4 h, concentrate, and dissolve in DMF (5.0 mL). Add this solution to a suspension of NaH (62.5 mg, 1.6 mmol) and 2-(4-chloro-phenyl)-5-(4-hydroxy-3-methoxy-phenyl)-5H-thiazolo[5,4-c]pyridin-4-one (200.0 mg, 0.5 mmol) in DMF (5 mL). Stir at room temperature for 2 h, dilute with water, and extract with CH2Cl2 (2×). Combine the organics, dry, and concentrate. Purify by flash chromatography, using 0-10% 2N NH3/MeOH in CH2Cl2, to give the title compound (100.0 mg, 40%). MS (ES+) 481.0 (M+1)+. 1H NMR (400 MHz, CDCl3): δ7.90 (d, 2H, J=8.4 Hz), 7.44 (d, 2H, J=4.0 Hz), 7.41 (s, 1H), 7.07 (s, 1H), 6.97 (d, 1H, J=8.8 Hz), 6.94 (d, 1H, J=2.2 Hz), 6.81 (dd, 1H, J=8.6, 2.4 Hz), 5.04 (s, 2H), 4.07 (t, 2H, J=7.0 Hz), 3.83 (s, 3H), 3.72 (s, 3H), 3.27 (t, 2H, J=6.8 Hz).

Provenance & Evidence