Ethyl Acetate → HCID 24805140, compound

HRID 1692712Notes

Reaction equation

HRID 1692712 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]#[N:8].CN(C)[CH:11]=[CH:12][C:13]([C:15]1[CH:16]=[CH:17][C:18]([F:26])=[C:19]([N:21]([CH3:25])[C:22](=[O:24])[CH3:23])[CH:20]=1)=O.C(OCC)(=O)C>C(O)(=O)C>[F:26][C:18]1[CH:17]=[CH:16][C:15]([C:13]2[N:6]3[N:5]=[CH:4][C:3]([C:7]#[N:8])=[C:2]3[N:1]=[CH:11][CH:12]=2)=[CH:20][C:19]=1[N:21]([CH3:25])[C:22](=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 855155-Amino-4-cyanopyrazoleHCID 66990275HCID 66990275, compound

Product 1

HCID 24805140HCID 24805140, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.041 g (0.38 mmol) of 5-amino-1H-pyrazole-4-carbonitrile and 0.1 g (0.38 mmol) of N-[5-(3-dimethylamino-acryloyl)-2-fluoro-phenyl]-N-methyl-acetamide in 10 mL of glacial acetic acid was refluxed for 2.5 hours and then the solvent was removed by reduced pressure distillation. Dichloromethane (15 mL) and a saturated sodium bicarbonate solution (10 mL) were added to the resulting residue. The two layers were separated, and the aqueous layer was washed with 10 mL of dichloromethane. The organic layers were washed with 10 mL of water and dried over magnesium sulfate. The dichloromethane layer was evaporated to dryness to yield an oil which, in the presence of ethyl acetate, gave 95 mg of N-{2-fluoro-5-[3-cyano-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-methyl-acetamide as a solid (yield 81%).

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. customthe solvent was removed by reduced pressure distillation
  3. additionDichloromethane (15 mL) and a saturated sodium bicarbonate solution (10 mL) were added to the resulting residue
  4. customThe two layers were separated
  5. washthe aqueous layer was washed with 10 mL of dichloromethane
  6. washThe organic layers were washed with 10 mL of water
  7. dry with materialdried over magnesium sulfate
  8. customThe dichloromethane layer was evaporated to dryness
  9. customto yield an oil which

Sources & evidence

ORD record
ord-752abd3e364c4b0ca51787142b3ce207
Source dataset
uspto-grants-2012_04
Patent number
US08158632B2

Reaction notes

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