Hydrochloric Acid → 4-chloro-N-[5-chloro-2-(2-methanesulfonylamino-benzoyl)-pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide

HRID 1898048Notes

Reaction equation

HRID 1898048 reaction equation
[NH2:1][C:2]1[CH:34]=[CH:33][CH:32]=[CH:31][C:3]=1[C:4]([C:6]1[C:11]([N:12]([CH2:27][O:28][CH3:29])[S:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([C:23]([F:26])([F:25])[F:24])[CH:17]=2)(=[O:15])=[O:14])=[CH:10][C:9]([Cl:30])=[CH:8][N:7]=1)=[O:5].[CH3:35][S:36](Cl)(=[O:38])=[O:37].Cl.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>N1C=CC=CC=1>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([S:13]([N:12]([C:11]2[C:6]([C:4](=[O:5])[C:3]3[CH:31]=[CH:32][CH:33]=[CH:34][C:2]=3[NH:1][S:36]([CH3:35])(=[O:38])=[O:37])=[N:7][CH:8]=[C:9]([Cl:30])[CH:10]=2)[CH2:27][O:28][CH3:29])(=[O:15])=[O:14])=[CH:17][C:18]=1[C:23]([F:26])([F:25])[F:24]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 31297Methanesulfonyl chlorideHCID 2724141Tetrabutylammonium FluorideHCID 57942208N-[2-(2-amino-benzoyl)-5-chloro-pyridin-3-yl]-4-chloro-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide

Product 1

HCID 666489504-chloro-N-[5-chloro-2-(2-methanesulfonylamino-benzoyl)-pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred suspension of N-[2-(2-amino-benzoyl)-5-chloro-pyridin-3-yl]-4-chloro-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide in pyridine (1 mL) was added methanesulfonyl chloride (26 mg, 0.226 mmol). After 2 h the reaction mixture was poured into 1 M HCl and the aqueous portions were subsequently extracted with EtOAc. The combined extracts were dried and concentrated under reduced pressure. The resulting residue was dissolved in THF (5 mL), treated with TBAF (1 M in THF, 200 L, 0.200 mmol), and then stirred at room temperature for 3-4 h. The reaction mixture was subsequently poured into 1 M HCl and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure to provide 4-chloro-N-[5-chloro-2-(2-methanesulfonylamino-benzoyl)-pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide. MS m/z: 634.0 (M+Na).

Workup

  1. extractionthe aqueous portions were subsequently extracted with EtOAc
  2. customThe combined extracts were dried
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting residue was dissolved in THF (5 mL)
  5. extractionthe aqueous layer was extracted with EtOAc
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-23db530ae3754f0daf59c473afed0d2b
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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