Water → HCID 86760491, compound

HRID 1354182Notes

Reaction equation

HRID 1354182 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:23][CH:22]=3)=[C:11]3[CH:12]=[CH:13][C:14]([C:16]([F:19])([F:18])[F:17])=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl[C:32]([O:34][CH3:35])=[O:33].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH3:35][O:34][C:32](=[O:33])[NH:30][S:27]([C:24]1[CH:25]=[CH:26][C:21]([C:20]2[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:9][N:10]3[CH:15]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:13]=[CH:12][C:11]=23)=[CH:22][CH:23]=1)(=[O:29])=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformate2×HCID 11430Potassium Carbonate2×HCID 9845828HCID 9845828, compound

Product 1

HCID 86760491HCID 86760491, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A Mixture of 4-[2-(3-fluoro-phenyl)-6-trifluoromethyl-pyrazolo[1,5-a]pyridin-3-yl]benzenesulfonamide (0.1 g 0.23 mmol), methyl chloroformate (Aldrich) (0.028 g 0.3 mmol) and potassium carbonate (0.07 g 0.05 mmol) were stirred and heated at reflux under nitrogen in acetone (10 ml) for 18 hr. Additional methyl chloroformate (0.028 g) and potassium carbonate (0.07 g) were added and heating continued for a further 24 hr. The reaction mixture was poured into water (100 ml) and extracted with ethyl acetate (3×50 ml). The combined extracts were washed with brine (30 ml), dried (MgSO4) and the solvent removed. The residues were purified by SPE chromatography, elution with cyclohexane:ethyl acetate (3:1) gave the title compound as a white solid (0.03 g 26%). MH− 492

Workup

  1. temperatureheated
  2. temperatureheating
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. washThe combined extracts were washed with brine (30 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed
  7. customThe residues were purified by SPE chromatography, elution with cyclohexane:ethyl acetate (3:1)

Sources & evidence

ORD record
ord-680cae9eba96442295fc62da45588225
Source dataset
uspto-grants-2007_05
Patent number
US07223772B1

Reaction notes

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