Ethyl Acetate → HCID 24805142, compound

HRID 1692713Notes

Reaction equation

HRID 1692713 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]([Cl: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>[Cl: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 67279027N-[2-chloro-5-(3-dimethylamino-acryloyl)-phenyl]-N-methyl-acetamide

Product 1

HCID 24805142HCID 24805142, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.046 g (0.43 mmol) of 5-amino-1H-pyrazole-4-carbonitrile and 0.120 g (0.43 mmol) of N-[5-(3-dimethylamino-acryloyl)-2-chloro-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. To the resulting residue were added 15 mL of dichloromethane and 10 mL of saturated sodium bicarbonate solution. 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 108 mg of N-{2-chloro-5-[3-cyano-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-methyl-acetamide as a solid (yield 77%).

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. customthe solvent was removed by reduced pressure distillation
  3. additionTo the resulting residue were added 15 mL of dichloromethane and 10 mL of saturated sodium bicarbonate solution
  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-60d86286c5db4d7fae67b3ff9bf4c638
Source dataset
uspto-grants-2012_04
Patent number
US08158632B2

Reaction notes

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