Ethyl Acetate → N-[3-(3-cyano-pyrazolo[1,5-a]pyrimidin-7-yl)-phenyl]-N-ethyl-methanesulfonamide

HRID 550561

반응식

HRID 550561 반응식
[C:1]([C:3]1[CH:7]=[N:6][NH:5][C:4]=1[NH2:8])#[N:2].CN(C)[CH:11]=[CH:12][C:13]([C:15]1[CH:16]=[C:17]([N:21]([CH2:26][CH3:27])[S:22]([CH3:25])(=[O:24])=[O:23])[CH:18]=[CH:19][CH:20]=1)=O.C(OCC)(=O)C>C(O)(=O)C>[C:1]([C:3]1[CH:7]=[N:6][N:5]2[C:13]([C:15]3[CH:16]=[C:17]([N:21]([CH2:26][CH3:27])[S:22]([CH3:25])(=[O:24])=[O:23])[CH:18]=[CH:19][CH:20]=3)=[CH:12][CH:11]=[N:8][C:4]=12)#[N:2]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 855155-Amino-4-cyanopyrazoleHCID 67198287N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl)-N-ethyl-methanesulfonamide

생성물 1

HCID 11653036N-[3-(3-cyano-pyrazolo[1,5-a]pyrimidin-7-yl)-phenyl]-N-ethyl-methanesulfonamide수율 52.4%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A mixture of 0.196 g (1.82 mmol) of 4-cyano-2H-pyrazol-3-ylamine and 0.54 g (1.82 mmol) of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-ethyl-methanesulfonamide in 10 ml of glacial acetic acid was refluxed for 8 hours and then the solvent was removed by reduced pressure distillation. To the resulting residue were added 10 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 324 mg of N-[3-(3-cyano-pyrazolo[1,5-a]pyrimidin-7-yl)-phenyl]-N-ethyl-methanesulfonamide as a yellow solid (yield 52.4%).

후처리

  1. temperaturewas refluxed for 8 hours
  2. customthe solvent was removed by reduced pressure distillation
  3. additionTo the resulting residue were added 10 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

출처 및 근거

ORD 기록
ord-e032f0561f5749b7b00f522d40231695
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947688B2

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