2,5-Difluorobenzenesulfonyl chloride → N-(3-{4-[2-(ethylamino)pyrimidin-4-yl]-1-(4-methoxybenzyl)-1H-pyrazol-3-yl}phenyl)-2,5-difluorobenzenesulfonamide

HRID 1843672Notes

Reaction equation

HRID 1843672 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][CH2:20][CH3:21])[N:14]=3)=[CH:11][N:10]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[F:31][C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=1[S:39](Cl)(=[O:41])=[O:40].[Na]>N1C=CC=CC=1>[CH2:20]([NH:19][C:15]1[N:14]=[C:13]([C:12]2[C:8]([C:4]3[CH:3]=[C:2]([NH:1][S:39]([C:33]4[CH:34]=[C:35]([F:38])[CH:36]=[CH:37][C:32]=4[F:31])(=[O:41])=[O:40])[CH:7]=[CH:6][CH:5]=3)=[N:9][N:10]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=3)[CH:11]=2)[CH:18]=[CH:17][N:16]=1)[CH3:21]

Participants

5

Reactant 3

HCID 27369112,5-Difluorobenzenesulfonyl chlorideHCID 5360545SodiumHCID 671848314-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-N-ethylpyrimidin-2-amine

Product 1

HCID 67185037N-(3-{4-[2-(ethylamino)pyrimidin-4-yl]-1-(4-methoxybenzyl)-1H-pyrazol-3-yl}phenyl)-2,5-difluorobenzenesulfonamideYield 91.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

340 mg (0.85 mmol) of 4-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-N-ethylpyrimidin-2-amine were dissolved in 10 ml of dry pyridine and 114 μl (0.85 mmol) of 2,5-difluorobenzensulfonyl chloride were added. The resulting solution was stirred at room temperature overnight. The mixture was then poured into aqueous sodium hydrogenocarbonate and extracted with dichloromethane. The organic layer was finally dried over sodium sulphate and evaporated, giving 450 mg (91%) of the title compound.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was finally dried over sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-3f073333aa6e4406823f33d7c1579120
Source dataset
uspto-grants-2015_02
Patent number
US08946250B2

Reaction notes

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