Water → N-[2-(2-amino-pyridine-3-carbonyl)-5-chloro-pyridin-3-yl]-4-chloro-3-trifluoromethyl-benzenesulfonamide

HRID 419167Notes

Reaction equation

HRID 419167 reaction equation
C(OC(=O)[NH:7][C:8]1[C:13]([C:14]([C:16]2[C:21]([N:22]([S:26]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([C:36]([F:39])([F:38])[F:37])[CH:30]=3)(=[O:28])=[O:27])COC)=[CH:20][C:19]([Cl:40])=[CH:18][N:17]=2)=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=1)(C)(C)C.O>OS(O)(=O)=O.C(O)(C(F)(F)F)=O>[NH2:7][C:8]1[C:13]([C:14]([C:16]2[C:21]([NH:22][S:26]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([C:36]([F:39])([F:38])[F:37])[CH:30]=3)(=[O:28])=[O:27])=[CH:20][C:19]([Cl:40])=[CH:18][N:17]=2)=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 2

HCID 962WaterHCID 57942364HCID 57942364, compound

Product 1

HCID 57942096N-[2-(2-amino-pyridine-3-carbonyl)-5-chloro-pyridin-3-yl]-4-chloro-3-trifluoromethyl-benzenesulfonamideYield 48%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of (3-{5-chloro-3-[(4-chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carbonyl}-pyridin-2-yl)-carbamic acid tert-butyl ester (25 mg, 0.0394 mmol) in 5% H2SO4 in TFA (4 mL) and water (1 mL) was stirred at 50° C. for 6 h. The reaction mixture was cooled to room temperature, evaporated to dryness and treated with saturated aqueous NaHCO3 solution until pH 7-8. The mixture was extracted with EtOAc (2×15 mL), dried (anhydrous Na2SO4) and concentrated. The obtained residue was column purified to afford N-[2-(2-amino-pyridine-3-carbonyl)-5-chloro-pyridin-3-yl]-4-chloro-3-trifluoromethyl-benzenesulfonamide (9.3 mg) in 48% yield. ESMS m/z (relative intensity): 491 (M+H)+ (100).

Workup

  1. customevaporated to dryness
  2. additiontreated with saturated aqueous NaHCO3 solution until pH 7-8
  3. extractionThe mixture was extracted with EtOAc (2×15 mL)
  4. dry with materialdried (anhydrous Na2SO4)
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-ad91939add8d4636b3ed9a3896e4cf8a
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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