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Ozone → 6-{2-Oxo-4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1466143
ノート
印刷プレビュー

反応式

HRID 1466143 の反応式
O=[O+][O-].[CH2:4]([C:7]1[CH:16]=[CH:15][C:10]2[C:11](=[O:14])[O:12][CH2:13][C:9]=2[CH:8]=1)[CH:5]=C.[O:17]=[C:18]1[CH2:23][NH:22][CH2:21][CH2:20][N:19]1[CH:24]1[CH2:33][CH2:32][C:31]2[CH:30]=[C:29]([C:34]#[N:35])[CH:28]=[CH:27][C:26]=2[CH2:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[O:17]=[C:18]1[CH2:23][N:22]([CH2:5][CH2:4][C:7]2[CH:16]=[CH:15][C:10]3[C:11](=[O:14])[O:12][CH2:13][C:9]=3[CH:8]=2)[CH2:21][CH2:20][N:19]1[CH:24]1[CH2:33][CH2:32][C:31]2[CH:30]=[C:29]([C:34]#[N:35])[CH:28]=[CH:27][C:26]=2[CH2:25]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 24823OzoneHCID 5049666Sodium triacetoxyborohydrideHCID 666439845-allyl-2-benzofuran-1(3H)-oneHCID 895249666-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

生成物 1

HCID 715195886-{2-Oxo-4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Ozone was bubbled into a solution of 5-(prop-2-en-1-yl)-2-benzofuran-1(3H)-one (102 mg, 0.59 mmol) in DCM until the color changed to orange. Excess ozone was removed by bubbling nitrogen through the reaction, which was followed by addition of 6-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (50 mg, 0.20 mmol) and sodium triacetoxyborohydride (210 mg, 0.98 mmol). The reaction was allowed to stir at RT for 24 hours. The reaction was diluted with DCM, washed with brine, dried over MgSO4, and purified by prep-TLC to afford the title product. LC-MS (IE, m/z): 416 [M+1]+.

後処理

  1. customExcess ozone was removed
  2. customby bubbling nitrogen
  3. customthrough the reaction, which
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. custompurified by prep-TLC

出典と根拠

ORDレコード
ord-6916099c4bd04a83aa094c8fd56488be
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08999990B2

反応ノート

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