3-[bis(methylsulfanyl)methylene]-1-(cyclobutylmethyl)-2,4(1H,3H)-pyridinedione → N-{3-[1-(cyclobutylmethyl)-4-hydroxy-2-oxo-1,2-dihydro-3-pyridinyl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl}methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

A solution of the product of Example 468C (0.050 g, 0.176 mmol) in dioxane (5 mL) was treated with the product of Example 425D (0.030 g, 0.113 mmol), stirred at 110° C. for 1 hour, and cooled to 25° C. The solid precipitate was collected by filtration and dried to provide the title compound (0.018 g, 35%). 1H NMR (300 MHz, DMSO-d6) δ 1.88 (m, 6 H) 2.74 (dt, J=15.17, 7.68 Hz, 1 H) 3.08 (s, 3 H) 4.03 (d, J=7.35 Hz, 2 H) 6.32 (d, J=7.72 Hz, 1H) 7.56 (dd, J=8.82, 2.57 Hz, 1 H) 7.62 (d, J=2.21 Hz, 1 H) 7.66 (m, 1 H) 8.06 (d, J=7.35 Hz, 1 H) 10.24 (s, 1 H) 13.83 (s, 1 H) 14.28 (s, 1 H). MS (ESI−) m/z 451 (M−H)−.

Provenance & Evidence