Dimethylformamide → 4-(2,2-Difluorovinyl)-1-[(6-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)methyl]pyrrolidin-2-one

HRID 1896424노트

반응식

HRID 1896424 반응식
Cl[CH2:2][C:3]1[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5][N:6]2[CH:11]=[C:10]([CH3:12])[CH:9]=[N:8][C:7]=12.[F:19][C:20]([F:28])=[CH:21][CH:22]1[CH2:26][NH:25][C:24](=[O:27])[CH2:23]1.CN(C=O)C.[H-].[Na+]>O>[F:19][C:20]([F:28])=[CH:21][CH:22]1[CH2:26][N:25]([CH2:2][C:3]2[C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:5][N:6]3[CH:11]=[C:10]([CH3:12])[CH:9]=[N:8][C:7]=23)[C:24](=[O:27])[CH2:23]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 17948959HCID 17948959, 화합물HCID 577430083-(Chloromethyl)-6-methyl-2-phenylpyrazolo[1,5-a]pyrimidine

생성물 1

HCID 536291324-(2,2-Difluorovinyl)-1-[(6-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)methyl]pyrrolidin-2-one수율 50%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

The above mentioned solution of intermediate x146 is added to a solution containing 4-(2,2-difluorovinyl)pyrrolidin-2-one x98 (2.64 mmol, 1.1 eq, 0.356 g), 6 ml of dry DMF and sodium hydride (60% dispersion in oil, 2.64 mmol, 1.1 eq, 0.1 g) that have been stirred at room temperature for 0.5 hour. The resulting mixture is heated up at 80° C. for 1 hour. The mixture is poured in water and extracted with AcOEt. The cumulated organic layers are washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure. The residue is crystallized in AcOEt to afford 0.443 g of 4-(2,2-difluorovinyl)-1-[(6-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)methyl]pyrrolidin-2-one 211.

후처리

  1. additionis added to a solution
  2. temperatureThe resulting mixture is heated up at 80° C. for 1 hour
  3. extractionextracted with AcOEt
  4. washThe cumulated organic layers are washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue is crystallized in AcOEt

출처 및 근거

ORD 기록
ord-b57ff4dc73af4e6992559af31319064b
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518943B2

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