5-chloro-4-[4-chloro-2-(2-cyanopyridin-4-yl)phenoxy]-N-(2,4-dimethoxybenzyl)-2-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide → 4-{2-[2-(aminomethyl)pyridin-4-yl]-4-chlorophenoxy}-5-chloro-2-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

HRID 46247Notes

Reaction equation

HRID 46247 reaction equation
[Cl:1][C:2]1[C:3]([O:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[C:37]2[CH:42]=[CH:41][N:40]=[C:39]([C:43]#[N:44])[CH:38]=2)=[CH:4][C:5]([F:28])=[C:6]([S:8]([N:11](CC2C=CC(OC)=CC=2OC)[C:12]2[S:16][N:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:7]=1>CO.O1CCOCC1.[Ni]>[NH2:44][CH2:43][C:39]1[CH:38]=[C:37]([C:31]2[CH:32]=[C:33]([Cl:36])[CH:34]=[CH:35][C:30]=2[O:29][C:3]2[C:2]([Cl:1])=[CH:7][C:6]([S:8]([NH:11][C:12]3[S:16][N:15]=[CH:14][N:13]=3)(=[O:9])=[O:10])=[C:5]([F:28])[CH:4]=2)[CH:42]=[CH:41][N:40]=1

Participants

5

Reactant 1

HCID 594364755-chloro-4-[4-chloro-2-(2-cyanopyridin-4-yl)phenoxy]-N-(2,4-dimethoxybenzyl)-2-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

Product 1

HCID 468410824-{2-[2-(aminomethyl)pyridin-4-yl]-4-chlorophenoxy}-5-chloro-2-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamideYield 10%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

5-chloro-4-[4-chloro-2-(2-cyanopyridin-4-yl)phenoxy]-N-(2,4-dimethoxybenzyl)-2-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 340, 0.04 g, 0.00006 mol) was partially dissolved in methanol (5.0 mL) and 1,4-dioxane (5.0 mL). The solution was passed through an H-Cube™ at 70° C. with Raney nickel catalyst (30 mm cartridge) 3 times eluting with methanol to get complete conversion. Concentration in vacuo afforded the title compound as a colourless solid, 0.004 g, 10% yield.

Workup

  1. washeluting with methanol
  2. customto get complete conversion
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-5b620114122a48e9b95337dcee620503
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

Loading…