2,5-Difluorobenzenesulfonyl chloride → 2,5-difluoro-N-(3-{1-(4-methoxybenzyl)-4-[2-(methylamino)-pyridin-4-yl]-1H-pyrazol-3-yl}phenyl)benzenesulfonamide

HRID 45868Notes

Reaction equation

HRID 45868 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH3:20])[CH:14]=3)=[CH:11][N:10]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[F:30][C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=1[S:38](Cl)(=[O:40])=[O:39].[Na]>N1C=CC=CC=1>[F:30][C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=1[S:38]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH3:20])[CH:14]=3)=[CH:11][N:10]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=3)[N:9]=2)[CH:3]=1)(=[O:40])=[O:39]

Participants

5

Reactant 3

HCID 27369112,5-Difluorobenzenesulfonyl chlorideHCID 5360545SodiumHCID 671862484-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-N-methylpyridin-2-amine

Product 1

HCID 671845852,5-difluoro-N-(3-{1-(4-methoxybenzyl)-4-[2-(methylamino)-pyridin-4-yl]-1H-pyrazol-3-yl}phenyl)benzenesulfonamideYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

250 mg (0.65 mmol) of 4-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-N-methylpyridin-2-amine (prepared as described in Example 29) were dissolved in 10 ml of dry pyridine and 87 μl of 2,5-difluorobenzensulfonylchloride were added The reaction was stirred at room temperature overnight, then poured into aqueous sodium hydrogenocarbonate and extracted with dichloromethane. The organic layer was dried over sodium sulphate and evaporated in vacuo. The residue was then triturated with diethylether, giving 300 mg of the title compound (82%).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. customevaporated in vacuo
  4. customThe residue was then triturated with diethylether

Sources & evidence

ORD record
ord-2af413c8ee3e47f2b7e6f1e9b9e52d3d
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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