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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
ノート
印刷プレビュー

反応式

HRID 2059943 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 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]propanoate収率 90.6%

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-59232db235b44a3c9fc00d66010d15b9
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08278324B2

反応ノート

読み込み中…

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