Triethylamine → HCID 178479863, compound

Participants

Reaction Conditions

Reaction Steps

2-{1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido-1,3-dihydro-2,1,3-benzothiadiazol-5-yl}-4-(hydroxymethyl)benzonitrile (4-3) (30 mg, 0.07 mmol, 1 eq) was dissolved in NMP (1 mL) and triethylamine (0.03 mL, 0.22 mmol, 3 eq) was added followed by mesyl chloride (0.006 mL, 0.08 mmil, 1.1 eq). After 10 minutes, 4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridin-3-ol (23.2 mg, 0.16 mmol, 2 eq) and DIPEA (0.085 mL, 0.49 mmol, 6 eq) were added. The resulting mixture stirred at 80° C. for 1 h. The mixture was cooled and 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-[(3-hydroxy-6,7-dihydroisoxazolo[4,5-c]pyridin-5(4H)-yl)methyl]benzonitrile (20-1) as a white solid. HRMS m/z (M+H) 528.1521 found, 528.1512 required.

Provenance & Evidence