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Dicyclohexylcarbodiimide → 3-(4-(2-(4-Ethoxy-4-oxobutoxy)phenyl)piperazin-1-yl)propyl 2-oxo-1,2,3,4-tetrahydroquinoline-7-carboxylate

HRID 887070
ノート
印刷プレビュー

反応式

HRID 887070 の反応式
[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([C:12]([OH:14])=[O:13])=[CH:7][CH:8]=2)[NH:3]1.O[CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:39]=[CH:38][CH:37]=[CH:36][C:26]=2[O:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:21][CH2:20]1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C1COCC1>[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([C:12]([O:14][CH2:16][CH2:17][CH2:18][N:19]3[CH2:20][CH2:21][N:22]([C:25]4[CH:39]=[CH:38][CH:37]=[CH:36][C:26]=4[O:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:23][CH2:24]3)=[O:13])=[CH:7][CH:8]=2)[NH:3]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 3

HCID 10868DicyclohexylcarbodiimideHCID 132430012-Oxo-1,2,3,4-tetrahydroquinoline-7-carboxylic acidHCID 57420184Ethyl 4-(2-(4-(3-hydroxypropyl)piperazin-1-yl)phenoxy)butanoate

生成物 1

HCID 574201853-(4-(2-(4-Ethoxy-4-oxobutoxy)phenyl)piperazin-1-yl)propyl 2-oxo-1,2,3,4-tetrahydroquinoline-7-carboxylate

試薬・触媒・溶媒 2

HCID 14284
4-(Dimethylamino)pyridine
触媒
HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2-oxo-1,2,3,4-tetrahydroquinoline-7-carboxylic acid 22 (0.21 g, 0.001 mol), ethyl 4-(2-(4-(3-hydroxypropyl)piperazin-1-yl)phenoxy)butanoate 27 (0.38 g, 0.001 mol), dicyclohexylcarbodiimide (0.21 g, 0.001 mol), 4-(dimethylamino)pyridine (0.12 g, 0.001 mol) in 20 mL THF was stirred at room temperature for 12 hours. The progress of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was evaporated; the residue was diluted with DCM (25 mL). The filtrate was washed with saturated aqueous NaHCO3 solution (25 mL×2) and water (25 mL×2), dried over sodium sulfate (Na2SO4) and evaporated. The residue was purified by silica gel column chromatography using 0-100% gradient of hexane and ethyl acetate to give the pure 3-(4-(2-(4-ethoxy-4-oxobutoxy)phenyl)piperazin-1-yl)propyl 2-oxo-1,2,3,4-tetrahydroquinoline-7-carboxylate 28. Colorless oil, 0.075 g (13%). 1H NMR (400 MHz, CDCl3): δ 1.21 (t, J=7.2 Hz, 3H); 1.99 (quintet, J=7.2 Hz, 2H); 2.13 (quintet, J=7.2 Hz, 2H); 2.50-2.65 (m, 8H); 2.99 (t, J=7.6 Hz, 4H); 3.08 (broad s, 4H); 4.01 (t, J=6.4 Hz, 2H); 4.12 (q, J=7.2 Hz, 2H); 4.38 (t, J=6.4 Hz, 2H); 6.81-6.89 (m, 4H); 7.20 (d, J=8.0 Hz, 1H); 7.50 (d, J=1.6 Hz, 1H); 7.64 (dd, J=1.6, 8.0 Hz, 1H, 9.00 (broad s, 1H). MS (ESI): m/z=524.50 (M+H+).

後処理

  1. customThe reaction mixture was evaporated
  2. additionthe residue was diluted with DCM (25 mL)
  3. washThe filtrate was washed with saturated aqueous NaHCO3 solution (25 mL×2) and water (25 mL×2)
  4. dry with materialdried over sodium sulfate (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-084218354279485fa59b293b77984a51
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08247420B2

反応ノート

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