Ethyl Acetate → HCID 57527230, compound

HRID 1452991Notes

Reaction equation

HRID 1452991 reaction equation
C([S:3]([C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:8]([C:13]2[C:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])=[N:15][N:16]([CH3:18])[CH:17]=2)[N:7]=1)(=O)=O)C.[C:26]([N:34]=[C:35]=S)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CCOC(C)=O>C1COCC1>[F:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:14]1[C:13]([C:8]2[N:7]=[C:6]3[S:3][C:35]([NH:34][C:26](=[O:33])[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[N:12][C:11]3=[CH:10][CH:9]=2)=[CH:17][N:16]([CH3:18])[N:15]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 68284Benzoyl isothiocyanateHCID 57527231HCID 57527231, compound

Product 1

HCID 57527230HCID 57527230, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(ethylsulfonyl)-6-(3-(2-fluorophenyl)-1-methyl-1H-pyrazol-4-yl)pyridine-3-amine (1.04 g, 2.89 mmol, 1.0 eq.) in THF under nitrogen at 0° C. was added benzoyl isothiocyanate (0.47 mL, 3.50 mmol, 1.2 eq.). The cold bath was removed, and the reaction mixture was stirred to room temperature for 20 min. It was then heated to 70° C. for 6 h. After cooling to room temperature, it was diluted with EtOAc and water. The layers were separated, and the organi layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Trituration with EtOAc afforded N-(5-(3-(2-fluorophenyl)-1-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridine-2-yl)benzamide as a light tan solid (1.05 g, 85% yield).

Workup

  1. customThe cold bath was removed
  2. temperatureIt was then heated to 70° C. for 6 h
  3. temperatureAfter cooling to room temperature
  4. additionit was diluted with EtOAc and water
  5. customThe layers were separated
  6. washthe organi layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a9297f637b604cc9bc8a4141f9eedfec
Source dataset
uspto-grants-2009_01
Patent number
US07473784B2

Reaction notes

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