Tetrahydrofuran → HCID 24996068, compound

HRID 1692137Notes

Reaction equation

HRID 1692137 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[C:19]([F:21])[C:18]([Cl:22])=[CH:17][C:16]=2[C:23]2[N:27]([CH3:28])[C:26]([CH2:29]C)=[N:25][N:24]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1COCC1.[NH4+:36].[OH-:37]>O.CCOC(C)=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[CH:20]=[C:19]([F:21])[C:18]([Cl:22])=[CH:17][C:16]=2[C:23]2[N:27]([CH3:28])[C:26]([C:29]([NH2:36])=[O:37])=[N:25][N:24]=2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 14923Ammonium HydroxideHCID 24996716HCID 24996716, compound

Product 1

HCID 24996068HCID 24996068, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a vial containing ethyl 5-[2-(4-tert-butyl-benzenesulfonylamino)-5-chloro-4-fluoro-phenyl]-4-methyl-4H-[1,2,4]triazole-3-carboxylic acid ethyl ester (synthesized according to general procedure C, 100 mg, 0.202 mmol) was added THF (2 mL) and 28% NH4OH in water (2 mL), and the resultant solution was stirred at room temperature for 1 h. The reaction mixture was subsequently diluted with EtOAc (30 mL) and the organics were washed with water (2×10 mL), dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography (50→100% gradient of EtOAc in hexanes). The pure fractions were collected and the solvent was removed. The isolated product was dissolved in MeCN/H2O and the solvent removed via lyophilization to afford the title compound as a white powder: MS (ES) M+H expected 466.0, found 466.0.

Workup

  1. washthe organics were washed with water (2×10 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography (50→100% gradient of EtOAc in hexanes)
  5. customThe pure fractions were collected
  6. customthe solvent was removed
  7. dissolutionThe isolated product was dissolved in MeCN/H2O
  8. customthe solvent removed via lyophilization

Sources & evidence

ORD record
ord-f4072de535154d4b9c7d3671e452074f
Source dataset
uspto-grants-2012_04
Patent number
US08153818B2

Reaction notes

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