Sodium Thiosulfate → N-{2-[5-chloro-3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carbonyl]-3-methoxy-phenyl}-2,2-dimethyl-propionamide

HRID 1438579Notes

Reaction equation

HRID 1438579 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:25][S:26]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([C:36]([F:39])([F:38])[F:37])[CH:30]=2)(=[O:28])=[O:27])[C:5]([CH:8]([OH:24])[C:9]2[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=2[NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[N:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:25][S:26]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([C:36]([F:39])([F:38])[F:37])[CH:30]=2)(=[O:27])=[O:28])[C:5]([C:8]([C:9]2[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=2[NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[O:24])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57942304N-(2-{[5-chloro-3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridin-2-yl]-hydroxy-methyl}-3-methoxy-phenyl)-2,2-dimethyl-propionamide

Product 1

HCID 66649350N-{2-[5-chloro-3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carbonyl]-3-methoxy-phenyl}-2,2-dimethyl-propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(2-{[5-chloro-3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridin-2-yl]-hydroxy-methyl}-3-methoxy-phenyl)-2,2-dimethyl-propionamide (0.17 g, 0.33 mmol) and Dess-Martin reagent (0.185 g, 0.44 mmol) in CH2Cl2 (10 mL) at room temperature was stirred for 5 h. A mixture of 10% aqueous Na2S2O3 (10 mL) and saturated aqueous NaHCO3 (10 mL) was then added and the biphasic mixture vigorously stirred for 30 min. The organic phase was then separated and the aqueous portion was extracted with CH2Cl2. The combined organic extracts were washed with saturated aqueous NaHCO3 and brine, dried (Na2SO4), and filtered. The filtrate was concentrated under reduced pressure and the residue purified by chromatography on silica gel using ethyl acetate-hexane to provide N-{2-[5-chloro-3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carbonyl]-3-methoxy-phenyl}-2,2-dimethyl-propionamide: MS m/z 604.0 (M+H)+.

Workup

  1. additionwas then added
  2. stirringthe biphasic mixture vigorously stirred for 30 min
  3. customThe organic phase was then separated
  4. extractionthe aqueous portion was extracted with CH2Cl2
  5. washThe combined organic extracts were washed with saturated aqueous NaHCO3 and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-71327088739b4f42a3ca32601fabab37
Source dataset
uspto-grants-2009_11
Patent number
US07622583B2

Reaction notes

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