Triethylamine → HCID 67408811, compound

Participants

Reaction Conditions

Reaction Steps

(6-{1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido-1,3-dihydro-2,1,3-benzothiadiazol-5-yl}-5-methylpyridin-2-yl)methanol (26-6) (25 mg, 0.06 mmol, 1 eq) was dissolved in NMP (0.5 mL) and triethylamine (0.03 mL, 0.18 mmol, 3.0 eq) was added followed by mesyl chloride (0.01 mL, 0.12 mmol, 2.0 eq). After 10 minutes, 1-(methylsulfonyl)piperazine (20.8 mg, 0.13 mmol, 2.0 eq) and DIPEA (0.033 mL, 0.19 mmol, 3.0 eq) were added. The resulting mixture stirred at 80° C. for 10 minutes. The mixture was cooled and purified by reverse phase chromatography (Waters Sunfire MSC18, 15-65% acetonitrile in water with 0.1% TFA modifier) to afford 1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-5-(3-methyl-6-{[4-(methylsulfonyl)piperazin-1-yl]methyl}pyridin-2-yl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (26-7) as a white solid. 1H NMR (400 MHz, CD3OD): δ 7.91 (d, J=7.6 Hz, 1 H); 7.48 (d, J=7.6 Hz, 1 H); 7.25 (dd, J=1.6, 8.4 Hz, 1 H); 7.19 (s, 1 H); 7.13 (d, J=8.0 Hz, 1 H); 4.53 (s, 2 H); 3.97 (d, J=7.2 Hz, 2 H); 3.56 (m, 4 H); 3.49 (m, 4 H); 3.33 (s, 3 H); 2.95 (s, 3 H); 2.43 (s, 3 H); 2.21 (m, 1 H); 1.64 (m, 1 H); 1.42 (m, 1H). HRMS m/z (M+H) 542.1693 found, 542.1702 required.

Provenance & Evidence