Hydrochloric Acid → 5-chloro-3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carboxylic acid N-methyl-N-phenylamide

HRID 419055Notes

Reaction equation

HRID 419055 reaction equation
[CH3:1][N:2]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:3]([C:5]1[C:10]([N:11]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:19]=2)(=[O:17])=[O:16])COC)=[CH:9][C:8]([Cl:29])=[CH:7][N:6]=1)=[O:4].Cl>O.O1CCOCC1>[CH3:1][N:2]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:3]([C:5]1[C:10]([NH:11][S:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:19]=2)(=[O:17])=[O:16])=[CH:9][C:8]([Cl:29])=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 579425265-chloro-3-[(4-chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carboxylic acid N-methyl-N-phenylamide

Product 1

HCID 579420855-chloro-3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carboxylic acid N-methyl-N-phenylamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

5-Chloro-3-[(4-chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carboxylic acid N-methyl-N-phenylamide (132 mg, 0.24 mmol) was magnetically stirred in water (1.0 mL) and 4N HCl in dioxane (2.5 mL) and heated at 85° C. (oil bath) for 7 h. LCMS indicated complete reaction; the reaction was concentrated and the residue was neutralized (pH 7) with aqueous sodium bicarbonate and the aqueous layer was extracted with EtOAc (3×80 mL). The extracts were dried (MgSO4), filtered, and chromatographed on silica gel using ethyl acetate-hexane gradient (0:100 to 50:50) to provide 5-chloro-3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carboxylic acid N-methyl-N-phenylamide. MS m/z: 504.1 (M+H).

Workup

  1. customreaction
  2. concentrationthe reaction was concentrated
  3. extractionthe aqueous layer was extracted with EtOAc (3×80 mL)
  4. dry with materialThe extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customchromatographed on silica gel

Sources & evidence

ORD record
ord-6ae2a4a93e3e402099531fca37630008
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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