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Phenol → 2-(2-chlorobenzoyl)-3-(2-phenoxy-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

HRID 1455262
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HRID 1455262 반응식
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Cl:10][C:11]1[CH:37]=[CH:36][CH:35]=[CH:34][C:12]=1[C:13]([C:15]1[C:22](=[O:23])[N:18]2[CH2:19][CH2:20][CH2:21][N:17]2[C:16]=1[C:24]1[CH:29]=[CH:28][N:27]=[C:26](S(C)(=O)=O)[N:25]=1)=[O:14]>C1COCC1.C([O-])(O)=O.[Na+]>[Cl:10][C:11]1[CH:37]=[CH:36][CH:35]=[CH:34][C:12]=1[C:13]([C:15]1[C:22](=[O:23])[N:18]2[CH2:19][CH2:20][CH2:21][N:17]2[C:16]=1[C:24]1[CH:29]=[CH:28][N:27]=[C:26]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:25]=1)=[O:14]
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참가 물질

6

반응물 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 574381012-(2-chlorobenzoyl)-3-(2-methanesulfonyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

생성물 1

HCID 114646442-(2-chlorobenzoyl)-3-(2-phenoxy-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회
HCID 516892
Sodium Bicarbonate
용매

실험 절차

To a solution of phenol (0.04 g, 0.43 mmol) in THF (1 mL) is added sodium hydride (0.02 g of a 60% dispersion in mineral oil, 0.32 mmol). After stirring 5 min at room temperature a solution of 2-(2-chloro-benzoyl)-3-(2-methanesulfonyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one, 24, (0.09 g, 0.21 mmol) in THF (2 mL) is added to the reaction mixture. After stirring 1.5 hours at room temperature, the mixture is diluted with aqueous saturated NaHCO3. The aqueous phase is extracted three times with CHCl3 and the combined organic phases are washed with aqueous saturated NaHCO3, dried (MgSO4), filtered and concentrated in vacuo. The crude residue is purified over silica (10% MeOH/CHCl3) to afford 30 mg of the desired product. 1H NMR (300 MHz, CDCl3) δ 8.77 (d, J=5.1 Hz, 1H), 8.04 (d, J=5.1 Hz, 1H), 7.49 (t, J=7.8 Hz, 1H), 7.41-7.20 (m, 9H), 4.00 (t, J=7.2 Hz, 2H), 3.95 (t, J=7.2 Hz, 2H), 2.54 (dddd, J=7.5, 7.5, 7.5, 7.5 Hz, 2H); ESI− MS: m/z (rel intensity) 431.1 (100, M+−H).

후처리

  1. additionis added to the reaction mixture
  2. extractionThe aqueous phase is extracted three times with CHCl3
  3. washthe combined organic phases are washed with aqueous saturated NaHCO3
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue is purified over silica (10% MeOH/CHCl3)

출처 및 근거

ORD 기록
ord-a8d5aedf7aa546da9b8111f0b1e25d8f
출처 데이터셋
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07482356B2

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