Benzeneacetic acid, 3,4-dimethoxy-, methyl ester → 6-(3,4-Dimethoxy-benzyl)-1-[1-(1-hydroxy-ethyl)-4-phenyl-butyl]-3-ethyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

HRID 566342

반응식

HRID 566342 반응식
[NH2:1][C:2]1[N:6]([CH:7]([CH:17]([OH:19])[CH3:18])[CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=[C:4]([CH2:20][CH3:21])[C:3]=1[C:22]([NH2:24])=[O:23].CC(C)([O-])C.[K+].[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH2:41][C:42](OC)=O)[CH:36]=[CH:37][C:38]=1[O:39][CH3:40].C1CCCCC1.C(OCC)(=O)C>C(O)C>[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[CH2:41][C:42]1[NH:24][C:22](=[O:23])[C:3]2[C:4]([CH2:20][CH3:21])=[N:5][N:6]([CH:7]([CH:17]([OH:19])[CH3:18])[CH2:8][CH2:9][CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:2]=2[N:1]=1

참가 물질

6

반응물 4

HCID 85213Benzeneacetic acid, 3,4-dimethoxy-, methyl esterHCID 212660795-amino-1-[1-(1-hydroxy-ethyl)-4-phenyl-butyl]-3-ethyl-1H-pyrazole-4-carboxamideHCID 21867204Cyclohexane ethylacetate2회HCID 23665647Potassium tert-butoxide

생성물 1

HCID 1357028686-(3,4-Dimethoxy-benzyl)-1-[1-(1-hydroxy-ethyl)-4-phenyl-butyl]-3-ethyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

1.0 g (3.03 mmol) of 5-amino-1-[1-(1-hydroxy-ethyl)-4-phenyl-butyl]-3-ethyl-1H-pyrazole-4-carboxamide, 1.60 g of potassium tert-butoxide and 1.40 g (19 mmol) of methyl 3,4-dimethoxyphenylacetate are refluxed overnight in 20 ml of ethanol. The solvent is removed in vacuo, the residue is taken up in dichloromethane, the mixture is extracted with 1N HCl, the organic phase is dried over Na2SO4 and evaporated on a rotary evaporator. Purification by chromatography (cyclohexane/EA=2:1, 1% formic acid) and separation of the diastereomers by chromatography gives 232 mg (16%) of the diastereomer which elutes more rapidly, Rf=0.2 (cyclohexane/ethyl acetate=2:1) and 150 mg (10%) of the diastereomer which elutes more slowly, Rf=0.15 (cyclohexane/ethyl acetate=2:1).

후처리

  1. customThe solvent is removed in vacuo
  2. extractionthe mixture is extracted with 1N HCl
  3. dry with materialthe organic phase is dried over Na2SO4
  4. customevaporated on a rotary evaporator
  5. customPurification
  6. customby chromatography (cyclohexane/EA=2:1, 1% formic acid) and separation of the diastereomers by chromatography
  7. customgives 232 mg (16%) of the diastereomer which

출처 및 근거

ORD 기록
ord-6a03ab62641d4043a3ee743ddf4826c8
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06174884B1

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