2,4-Difluorobenzenesulfonyl Chloride → HCID 59860190, compound

HRID 1625963Notes

Reaction equation

HRID 1625963 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[CH:18]=[C:19]([NH2:23])[CH:20]=[N:21][CH:22]=4)[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[F:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[S:32](Cl)(=[O:34])=[O:33]>N1C=CC=CC=1>[F:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[S:32]([NH:23][C:19]1[CH:20]=[N:21][CH:22]=[C:17]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[N:10]=[CH:9][CH:8]=[C:7]3[C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[CH:18]=1)(=[O:34])=[O:33]

Participants

4

Reactant 2

HCID 27342732,4-Difluorobenzenesulfonyl ChlorideHCID 59860221HCID 59860221, compound

Product 1

HCID 59860190HCID 59860190, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 5-[4-(4-pyridinyl)-6-quinolinyl]-3-pyridinamine (82 mg, 0.27 mmol) in anhydrous pyridine (2.0 ml) was treated with neat 2,4-difluorobenzenesulfonyl chloride in one portion. The reaction was stirred at room temperature for 30 minutes then was purified directly by prep-HPLC. The combined, desired fractions were evaporated under reduced pressure to remove organic solvents then diluted with small portions of brine and saturated aqueous sodium bicarbonate. The basic solution was extracted with ethyl acetate then the extracts were dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting colorless film was crystallized from methylene chloride and diethyl ether. The solids were collected by filtration, rinsed with diethyl ether then vacuum dried to afford the title compound (219 mg, 48%) as a white solid. MS(ES)+ m/e 475 [M+H]+.

Workup

  1. customthen was purified directly by prep-HPLC
  2. customdesired fractions were evaporated under reduced pressure
  3. customto remove organic solvents
  4. additionthen diluted with small portions of brine and saturated aqueous sodium bicarbonate
  5. extractionThe basic solution was extracted with ethyl acetate
  6. dry with materialthe extracts were dried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe resulting colorless film was crystallized from methylene chloride and diethyl ether
  9. filtrationThe solids were collected by filtration
  10. washrinsed with diethyl ether
  11. customvacuum dried

Sources & evidence

ORD record
ord-a97efe1bf2184266b70b5b7650ee77bc
Source dataset
uspto-grants-2014_07
Patent number
US08785433B2

Reaction notes

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