Pyridine → n-{3-[(4r)-1-Hydroxy-4-methyl-4-(3-methylbutyl)-3-oxo-3,4-dihydronaphthalen-2-yl]-1,1-dioxido-4h-1,2,4-benzothiadiazin-7-yl}-1h-benzimidazole-2-sulfonamide

Participants

Reaction Steps

A mixture of Example 39H (47.6 mg, 0.10 mmol), pyridine (64 mg, 0.80 mmol), and 2-benzimidazole sulfonyl chloride (87 mg, 0.40 mmol, prepared according to the procedure reported by S. M. Deshpande et al, J. Med. Chem. 1970,13, 143-144) in acetone (2 mL) was stirred at rt for 16 h. The reaction mixture was evaporated in vacuo and partitioned between ethyl acetate and water. The organic phase was separated, dried (MgSO4), filtered, and evaporated in vacuo. The residue was purified by chromatography on silica gel eluting with 99:1 dichloromethane/methanol to provide the title compound (28.0 mg, 45% yield). 1H NMR (300 MHz, DMSO-d6) δ 0.39 (m, 1H) 0.67 (d, J=6.62 Hz, 3H) 0.70 (d, J=6.62 Hz, 3H) 0.77 (m, 1H) 1.29 (m, 1H) 1.54 (s, 3H) 2.04 (m, 1H) 2.19 (m, 1H) 7.35 (dd, J=6.25, 2.94 Hz, 2H) 7.51 (m, 1H) 7.64 (m, 8H) 8.13 (d, J=7.72 Hz, 1H) 11.51 (s, 1H) 13.77 (s, 1H). MS (ESI+) m/z 620.0 (M+H)+, 641.9 (M+H−Na)+, (ESI−) m/z 618.0 (M−H)−.

Provenance & Evidence