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

HRID 601433Notes

Reaction equation

CS[C:3](SC)=[C:4]1[C:9](=[O:10])[CH:8]=[CH:7][N:6]([CH2:11][CH:12]2[CH2:15][CH2:14][CH2:13]2)[C:5]1=[O:16].[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:22][C:21]=1[S:31]([NH2:34])(=[O:33])=[O:32]>O1CCOCC1>[CH:12]1([CH2:11][N:6]2[CH:7]=[CH:8][C:9]([OH:10])=[C:4]([C:3]3[NH:19][C:20]4[CH:25]=[CH:24][C:23]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])=[CH:22][C:21]=4[S:31](=[O:33])(=[O:32])[N:34]=3)[C:5]2=[O:16])[CH2:13][CH2:14][CH2:15]1

Participants

Conditions

Temperature: 110 °C

Procedure

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)−.

Workup

temperaturecooled to 25° C
filtrationThe solid precipitate was collected by filtration
customdried

Sources & evidence

ORD record: ord-1bd169e2043d4a2f900d12f0507d91ab
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902203B2

Reaction notes

Loading…