4-chloro-N-[5-chloro-2-(2-nitro-benzoyl)-pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide → N-[2-(2-amino-benzoyl)-5-chloro-pyridin-3-yl]-4-chloro-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide

HRID 419041Notes

Reaction equation

HRID 419041 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:15]2[C:16]([C:22](=[O:32])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N+:29]([O-])=O)=[N:17][CH:18]=[C:19]([Cl:21])[CH:20]=2)[CH2:12][O:13][CH3:14])(=[O:10])=[O:9])=[CH:4][C:3]=1[C:33]([F:36])([F:35])[F:34]>CC(O)=O.[Fe]>[NH2:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:22]([C:16]1[C:15]([N:11]([CH2:12][O:13][CH3:14])[S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:33]([F:36])([F:35])[F:34])[CH:4]=2)(=[O:10])=[O:9])=[CH:20][C:19]([Cl:21])=[CH:18][N:17]=1)=[O:32]

Participants

4

Reactant 1

HCID 579423284-chloro-N-[5-chloro-2-(2-nitro-benzoyl)-pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide

Product 1

HCID 57942208N-[2-(2-amino-benzoyl)-5-chloro-pyridin-3-yl]-4-chloro-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Procedure

To a stirred suspension of Fe (376 mg, 6.73 mmol) in glacial AcOH (10 mL) at 80° C. was added a solution 4-chloro-N-[5-chloro-2-(2-nitro-benzoyl)-pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (700 mg, 1.34 mmol) in AcOH (5 mL) over 15 min. After complete addition, the mixture was stirred for 2 h and the progress of the reaction was followed by LCMS. Upon consumption of reactants, the reaction mixture was cooled to room temperature, diluted with EtOAc, and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and residue was partitioned with aqueous NaHCO3 and EtOAc. The organic portion was separated and the aqueous portion was extracted with EtOAc. The combined extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to provide N-[2-(2-amino-benzoyl)-5-chloro-pyridin-3-yl]-4-chloro-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide. MS m/z: 556.0 (M+Na).

Workup

  1. additionAfter complete addition
  2. customUpon consumption of reactants
  3. additiondiluted with EtOAc
  4. filtrationfiltered through a pad of Celite
  5. concentrationThe filtrate was concentrated under reduced pressure and residue
  6. customwas partitioned with aqueous NaHCO3 and EtOAc
  7. customThe organic portion was separated
  8. extractionthe aqueous portion was extracted with EtOAc
  9. dry with materialThe combined extracts were dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-5718a56417ce456cb0567cce06083918
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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