3-[bis(methylsulfanyl)methylene]-1-isopentyl-2,4(1H,3H)-pyridinedione → N-[3-(4-hydroxy-1-isopentyl-2-oxo-3-pyridyl)-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-7-yl]methanesulfonamide

HRID 601434Notes

Reaction equation

HRID 601434 reaction equation
CS[C:3](SC)=[C:4]1[C:9](=[O:10])[CH:8]=[CH:7][N:6]([CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[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>[OH:10][C:9]1[CH:8]=[CH:7][N:6]([CH2:11][CH2:12][CH:13]([CH3:14])[CH3:15])[C:5](=[O:16])[C:4]=1[C:3]1[NH:19][C:20]2[CH:25]=[CH:24][C:23]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])=[CH:22][C:21]=2[S:31](=[O:33])(=[O:32])[N:34]=1

Participants

4

Reactant 2

HCID 100395903-[bis(methylsulfanyl)methylene]-1-isopentyl-2,4(1H,3H)-pyridinedioneHCID 249506572-Amino-5-[(methylsulfonyl)amino]benzenesulfonamide

Product 1

HCID 136036674N-[3-(4-hydroxy-1-isopentyl-2-oxo-3-pyridyl)-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-7-yl]methanesulfonamideYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of the product of Example 457C (0.195 g, 0.68 mmol) in dioxane (10 mL) was reacted with the product of Example 425D (0.17 g, 0.64 mmol) at 115° C. for 1 hour. After cooling to about 25° C., the solid precipitate was collected by filtration and dried to provide the title compound (0.258 g, 89%). 1H NMR (300 MHz, DMSO-d6) δ 0.93 (d, J=6.25 Hz, 6 H) 1.58 (m, 3 H) 3.08 (s, 3 H) 3.99 (m, 2 H) 6.33 (d, J=6.62 Hz, 1 H) 7.57 (m, 2 H) 7.67 (d, J=8.82 Hz, 1 H) 8.07 (d, J=6.62 Hz, 1 H) 10.25 (s, 1 H) 13.84 (s, 1 H) 14.28 (s, 1 H). MS (ESI−) m/z 453 (M−H)−.

Workup

  1. filtrationthe solid precipitate was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-60ae66d4342a4dcb8c93cc6f7750354a
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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