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Ethyl Acrylate → Ethyl 3-[6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]propanoate

HRID 2059943
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HRID 2059943 반응식
FC(F)(F)C(O)=O.[CH3:8][CH:9]([O:11][C:12]1[CH:19]=[CH:18][C:17]([C:20]2[O:24][N:23]=[C:22]([C:25]3[C:26]([CH3:35])=[C:27]4[C:32](=[CH:33][CH:34]=3)[CH2:31][NH:30][CH2:29][CH2:28]4)[N:21]=2)=[CH:16][C:13]=1[C:14]#[N:15])[CH3:10].[C:36]([O:40][CH2:41][CH3:42])(=[O:39])[CH:37]=[CH2:38].N12CCCN=C1CCCCC2>C(#N)C>[C:14]([C:13]1[CH:16]=[C:17]([C:20]2[O:24][N:23]=[C:22]([C:25]3[C:26]([CH3:35])=[C:27]4[C:32](=[CH:33][CH:34]=3)[CH2:31][N:30]([CH2:38][CH2:37][C:36]([O:40][CH2:41][CH3:42])=[O:39])[CH2:29][CH2:28]4)[N:21]=2)[CH:18]=[CH:19][C:12]=1[O:11][CH:9]([CH3:8])[CH3:10])#[N:15]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8821Ethyl AcrylateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 575058522-[(1-Methylethyl)oxy]-5-[3-(5-methyl-1,2,3,4-tetrahydro-6-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile trifluoroacetate

생성물 1

HCID 57505851Ethyl 3-[6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]propanoate수율 90.6%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

A mixture of 2-[(1-methylethyl)oxy]-5-[3-(5-methyl-1,2,3,4-tetrahydro-6-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile trifluoroacetic acid salt (Example 11; 100 mg, 0.20 mmol), ethyl acrylate (31 mg, 33 μl, 0.31 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU; 187 mg, 185 μl, 1.23 mmol) in acetonitrile (3 ml) was stirred at room temperature for 3 hours. The solvent was evaporated and the residue dissolved in ethyl acetate (10 ml); the solution was washed with water (5 ml), dried and evaporated. Purification of the residue by chromatography on silica gel, eluting with 10% ethyl acetate in cyclohexane gave the title compound as a colourless oil (86 mg).

후처리

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate (10 ml)
  3. washthe solution was washed with water (5 ml)
  4. customdried
  5. customevaporated
  6. customPurification of the residue by chromatography on silica gel
  7. washeluting with 10% ethyl acetate in cyclohexane

출처 및 근거

ORD 기록
ord-59232db235b44a3c9fc00d66010d15b9
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08278324B2

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