Potassium Carbonate → HCID 71269549, compound

HRID 540772Notes

Reaction equation

HRID 540772 reaction equation
[CH2:1]([N:3]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][CH:10]=2)=[CH:6][C:5]([C:17]2[CH:18]=[C:19]([C:23]([NH:26][S:27]([CH2:30][C:31]([F:34])([F:33])[F:32])(=[O:29])=[O:28])([CH3:25])[CH3:24])[CH:20]=[CH:21][CH:22]=2)=[N:4]1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S([CH2:51][N+:52]#[C-:53])(=O)=O)=CC=1.[N+](CS(C1C=CC(C)=CC=1)(=O)=O)#[C-]>CO.O>[CH2:1]([N:3]1[C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[O:16][CH:53]=[N:52][CH:51]=3)=[CH:13][CH:14]=2)=[CH:6][C:5]([C:17]2[CH:18]=[C:19]([C:23]([NH:26][S:27]([CH2:30][C:31]([F:34])([F:32])[F:33])(=[O:28])=[O:29])([CH3:25])[CH3:24])[CH:20]=[CH:21][CH:22]=2)=[N:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 52913937HCID 52913937, compoundHCID 86677196HCID 86677196, compound

Product 1

HCID 71269549HCID 71269549, compoundYield 3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
22 °C

Procedure

N-(2-{3-[1-ethyl-5-(4-formylphenoxy)-1H-pyrazol-3-yl]phenyl}propan-2-yl)-2,2,2-trifluoroethanesulfonamide (340 mg, 0.69 mmol, 1 equiv) was added to a suspension of potassium carbonate (237 mg, 1.72 mmol, 2.5 equiv) stirring in MeOH (3.4 mL) at 22° C. 1-[(isocyanomethyl)sulfonyl]-4-methylbenzene isocyanomethyl 4-methylphenyl sulfone (161 mg, 0.82 mmol, 1.2 equiv) was added and the resulting mixture was stirred at 22° C. for 30 minutes. The reaction was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (0-40% EtOAc:Hex). Fractions were identified, combined and concentrated in vacuo but the isolated material was not pure. The residue was then purified by reversed phase HPLC (0-95% acetonitrile:water with 0.025% TFA). Pure fractions were identified, combined, basified with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title compound (3% yield). Calc'd (M+1)+: 535.1. Found: 535.1.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous ammonium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (0-40% EtOAc:Hex)
  6. concentrationconcentrated in vacuo
  7. customThe residue was then purified by reversed phase HPLC (0-95% acetonitrile:water with 0.025% TFA)
  8. extractionextracted with ethyl acetate
  9. washThe organic layer was washed with saturated aqueous sodium chloride
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-556b1942ee254301b418a12982b3548c
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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