2,5-Difluorobenzenesulfonyl chloride → HCID 67184347, compound

HRID 45879Notes

Reaction equation

HRID 45879 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]([NH2:19])[N:14]=3)=[CH:11][N:10]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=1[S:37](Cl)(=[O:39])=[O:38].[Na]>N1C=CC=CC=1>[NH2:19][C:15]1[N:14]=[C:13]([C:12]2[C:8]([C:4]3[CH:3]=[C:2]([NH:1][S:37]([C:31]4[CH:32]=[C:33]([F:36])[CH:34]=[CH:35][C:30]=4[F:29])(=[O:39])=[O:38])[CH:7]=[CH:6][CH:5]=3)=[N:9][N:10]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)[CH:11]=2)[CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 27369112,5-Difluorobenzenesulfonyl chlorideHCID 5360545SodiumHCID 671841854-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyrimidin-2-amine

Product 1

HCID 67184347HCID 67184347, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

175 mg (0.47 mmol) of 4-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-pyrimidin-2-amine were dissolved with 10 ml of dry pyridine and 63 μl of 2,5-difluorobenzensulfonylchloride were added under stirring. The solution was maintained at room temperature overnight. The reaction mixture was then poured into aqueous sodium hydrogenocarbonate and extracted with dichloromethane. The organic layer was dried over sodium sulphate and evaporated to dryness. The residue was purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3; from 9/1 to 8/2), giving 80 mg (31%) of the title compound.

Workup

  1. additionwere added
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customevaporated to dryness
  5. customThe residue was purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3; from 9/1 to 8/2)

Sources & evidence

ORD record
ord-c47355ab48f0463e9496ef0e25f8034a
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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