Chloromethyl Methyl Ether → HCID 67410329, compound

Participants

Reaction Steps

2-{1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido-1,3-dihydro-2,1,3-benzothiadiazol-5-yl}-4-hydroxybenzonitrile (12-2) (25 mg, 0.06 mmol, 1 eq) was dissolved in anhydrous DMF (0.5 mL) and sodium hydride (3.1 mg, 0.08 mmol, 1.2 eq, 60% in oil) was added. The resulting mixture was stirred at ambient temperature for 30 minutes and MOM-Cl (0.01 mL, 0.1 mmol, 2 eq) was added. The resulting mixture stirred at ambient temperature for 10 minutes. The crude mixture was purified by reverse phase chromatography (Waters Sunfire MSC18, 10-100% acetonitrile in water with 0.1% TFA modifier) to afford 2-{1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido-1,3-dihydro-2,1,3-benzothiadiazol-5-yl}-4-(methoxymethoxy)benzonitrile (16-1) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.68 (d, J=8.4 Hz, 1 H); 7.19 (dd, J=1.6, 8.0 Hz, 1 H); 7.11 (s, 1 H); 7.09 (dd, J=2.4, 8.8 Hz, 1 H); 6.95 (s, 1 H); 6.91 (d, J=8.0 Hz, 1 H); 5.26 (s, 2 H); 3.91 (d, J=6.8 Hz, 2 H); 3.50 (s, 3 H); 3.34 (s, 3 H); 2.11-2.19 (m, 1 H); 1.61-1.69 (m, 1 H); 1.36-1.44 (m, 1 H). LRMS m/z (M+H) 436.3 found, 436.1 required.

Provenance & Evidence