4-Chloro-3-(trifluoromethyl)benzenesulfonyl Chloride → HCID 11583838, compound

HRID 1897992Notes

Reaction equation

HRID 1897992 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:15])[C:5]([S:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][C:18]=1[C:27]([F:30])([F:29])[F:28]>N1C=CC=CC=1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:15][C:4]2[C:5]([S:8][C:9]3[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=3)=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)(=[O:24])=[O:25])=[CH:19][C:18]=1[C:27]([F:30])([F:28])[F:29]

Participants

4

Reactant 2

HCID 27807194-Chloro-3-(trifluoromethyl)benzenesulfonyl ChlorideHCID 57942576HCID 57942576, compound

Product 1

HCID 11583838HCID 11583838, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 5-chloro-2-(pyridin-4-ylsulfanyl)-pyridin-3-ylamine (100 mg, 0.42 mmol) in anhydrous pyridine (0.5 mL) was added drop wise a solution of 4-chloro-3-trifluoromethyl-benzenesulfonyl chloride (117 mg, 0.42 mmol) in pyridine (0.25 mL). The resulting mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated under reduced pressure and diluted with EtOAc and brine. The aqueous portion was separated and extracted with EtOAc. The combined extracts were dried (Na2SO4) filtered and concentrated under reduced pressure. The residue was treated with 0.3 M aqueous NaOH and washed with CH2Cl2. The aqueous portion was acidified with conc HCl to pH 3 and extracted with EtOAc. The combined extracts were dried (Na2SO4) filtered and concentrated under reduced pressure. The residue was separated by preparative HPLC (20→80% gradient of ACN-water) and pure product fractions were lyophilized to provide pure product as a solid. Mass spectrum m/z: 480.0 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with EtOAc and brine
  3. customThe aqueous portion was separated
  4. extractionextracted with EtOAc
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. additionThe residue was treated with 0.3 M aqueous NaOH
  9. washwashed with CH2Cl2
  10. extractionextracted with EtOAc
  11. dry with materialThe combined extracts were dried (Na2SO4)
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was separated by preparative HPLC (20→80% gradient of ACN-water) and pure product fractions
  15. customto provide pure product as a solid

Sources & evidence

ORD record
ord-a9fd058054f04301a1e0a1c261314fed
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

Loading…