Water → HCID 118497068, compound

HRID 522094Notes

Reaction equation

HRID 522094 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([Cl:31])=[C:12]([CH:30]=2)[C:13]([NH:15][C:16]2[N:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:19]=[C:18]([C:27]([NH2:29])=[O:28])[CH:17]=2)=[O:14])[C:5]([F:32])=[CH:4][CH:3]=1.[C:33](OC(=O)C)(=[O:35])[CH3:34].O.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C>[C:33]([NH:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([Cl:31])=[C:12]([CH:30]=2)[C:13]([NH:15][C:16]2[N:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:19]=[C:18]([C:27]([NH2:29])=[O:28])[CH:17]=2)=[O:14])[C:5]([F:32])=[CH:4][CH:3]=1)(=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 118456284HCID 118456284, compound

Product 1

HCID 118497068HCID 118497068, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-(5-(6-amino-3-fluoropyridin-2-yl)-2-chlorobenzamido)-1-phenyl-1H-pyrazole-3-carboxamide (Preparation 1, 23 mg, 0.05 mmol) in acetic acid (2 mL) was added acetic anhydride (0.5 mL) and the reaction was stirred at room temperature for 18 hours. The reaction was poured into water (50 mL) and basified by the addition of solid potassium carbonate. The aqueous solution was extracted with ethyl acetate (50 mL) and the organic layer was washed with brine (50 mL), dried over magnesium sulphate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 40-60% EtOAc in heptanes followed by trituration in TBME to afford the title compound as a white solid (10 mg, 40%).

Workup

  1. extractionThe aqueous solution was extracted with ethyl acetate (50 mL)
  2. washthe organic layer was washed with brine (50 mL)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified
  6. washeluting with 40-60% EtOAc in heptanes

Sources & evidence

ORD record
ord-5725e455e9034b83b86ad2a4a0e42903
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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