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Trifluoroacetic acid → 2-(6-Chloropyrimidin-4-yl)-4-(1H-imidazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one hydrochloride

HRID 562457
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HRID 562457 반응식
C[N:2]([CH:4]=[C:5]([N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1)[C:6]([O:8]CC)=O)C.[Cl:16][C:17]1[CH:22]=[C:21]([NH:23]N)[N:20]=[CH:19][N:18]=1.FC(F)(F)C(O)=O>C(O)C>[ClH:16].[Cl:16][C:17]1[N:18]=[CH:19][N:20]=[C:21]([N:23]2[C:6](=[O:8])[C:5]([N:11]3[CH:15]=[CH:14][N:13]=[CH:12]3)=[CH:4][NH:2]2)[CH:22]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 2472224-Chloro-6-hydrazinylpyrimidineHCID 66726242Ethyl 3-(N,N-dimethylamino)-2-(1H-imidazol-1-yl)acrylate

생성물 1

HCID 866352552-(6-Chloropyrimidin-4-yl)-4-(1H-imidazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one hydrochloride

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

10.0 g (47.8 mmol) of the compound from Example 5A and 8.3 g (57.3 mmol) of the compound from Example 11A are initially charged in 100 ml of ethanol, and 1.5 ml (2.2 g, 19.0 mmol) of trifluoroacetic acid are added. The mixture is stirred under reflux for 12 h. The precipitated crystals are filtered off, the filter residue is washed with ethanol and the intermediate is dried under reduced pressure overnight. The intermediate is then suspended in 20 ml of methanol, 100 ml of a 4 M solution of hydrogen chloride in dioxane are added and the mixture is stirred at RT for 1 h. The solid is filtered off, the filter residue is washed with dioxane, ethyl acetate and diisopropyl ether and the product is dried under reduced pressure. Yield: 4.6 g (32% of theory)

후처리

  1. temperatureunder reflux for 12 h
  2. filtrationThe precipitated crystals are filtered off
  3. washthe filter residue is washed with ethanol
  4. customthe intermediate is dried under reduced pressure overnight
  5. addition100 ml of a 4 M solution of hydrogen chloride in dioxane are added
  6. stirringthe mixture is stirred at RT for 1 h
  7. filtrationThe solid is filtered off
  8. washthe filter residue is washed with dioxane, ethyl acetate and diisopropyl ether
  9. customthe product is dried under reduced pressure

출처 및 근거

ORD 기록
ord-5f61fbcf3c9b4aaa9ba7f98d791a9927
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08067407B2

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