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Quipazine → Ethyl 2-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]cyclohex-1-enecarboxylate

HRID 1714783
ノート
印刷プレビュー

反応式

HRID 1714783 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=1[NH:12][C:13](=[O:19])[CH2:14][CH2:15][CH2:16][CH2:17]Br)=[O:5])[CH3:2].[N:20]1([C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=2)[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=1[NH:12][C:13](=[O:19])[CH2:14][CH2:15][CH2:16][CH2:17][N:23]1[CH2:24][CH2:25][N:20]([C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=2)[CH2:21][CH2:22]1)=[O:5])[CH3:2]
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 5011QuipazineHCID 8471TriethylamineHCID 23155883Ethyl 2-(5-bromopentanoylamino)cyclohex-1-enecarboxylate

生成物 1

HCID 23155633Ethyl 2-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]cyclohex-1-enecarboxylate収率 86%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 66.5 g of 2-(5-bromopentanoylamino)cyclohex-1-enecarboxylic acid ethyl ester as synthesized in above Step 7-1-C, 46.9 g of 2-piperazin-1-ylquinoline as synthesized in above Step 7-1-A, 22.3 g of triethylamine and 350 ml of toluene was heated under reflux for an overnight. The solvent was concentrated under reduced pressure, and ethyl acetate was added to the residue, followed by washing with saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and the solvent was concentrated under reduced pressure. The residue was purified on silica gel column chromatography (n-hexane:ethyl acetate:methanol=1:6:0.2) to provide 79.8 g (86%) of 2-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]cyclohex-1-enecarboxylic acid ethyl ester.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for an overnight
  3. concentrationThe solvent was concentrated under reduced pressure, and ethyl acetate
  4. additionwas added to the residue
  5. washby washing with saturated aqueous sodium hydrogencarbonate solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationthe solvent was concentrated under reduced pressure
  8. customThe residue was purified on silica gel column chromatography (n-hexane:ethyl acetate:methanol=1:6:0.2)

出典と根拠

ORDレコード
ord-448e2025bf1a413c86810a34b913aef0
出典データセット
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07799775B2

反応ノート

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