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2-Aminoquinoline → 3-{3,5-dimethyl-4-[6-(quinolin-2-ylcarbamoyl)-1H-indol-2-yl]-phenyl}-propionic acid methyl ester

HRID 1514957
ノート
印刷プレビュー

反応式

HRID 1514957 の反応式
[CH3:1][O:2][C:3]([CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[C:18]([C:23]([OH:25])=O)[CH:17]=3)=[C:9]([CH3:26])[CH:8]=1)=[O:4].[NH2:27][C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[I-].C[NH+]1CCN(CCC)C1>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([CH3:26])[C:10]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[C:18]([C:23](=[O:25])[NH:27][C:28]2[CH:37]=[CH:36][C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:29]=2)[CH:17]=3)=[C:11]([CH3:13])[CH:12]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 113792-AminoquinolineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 669660741-Methyl-3-propylimidazolinium iodideHCID 669662052-[4-(2-Methoxycarbonylethyl)-2,6-dimethylphenyl]-1H-indole-6-carboxylic acid

生成物 1

HCID 66965694
3-{3,5-dimethyl-4-[6-(quinolin-2-ylcarbamoyl)-1H-indol-2-yl]-phenyl}-propionic acid methyl ester

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
150 °C

実験手順

A mixture of 2-[4-(2-methoxycarbonylethyl)-2,6-dimethylphenyl]-1H-indole-6-carboxylic acid (600 mg, 1.71 mmol), 2-aminoquinoline (246 mg, 1.71 mmol), EDCI (491 mg, 2.56 mmol), HOBT (254 mg, 1.88 mmol) and 1-methyl-3-propylimidazolinium iodide (140 mg, 560 μmol) in THF (10 mL) was heated in a microwave apparatus at 150° C. for 3 h then the mixture was poured into ethyl acetate and extracted with water twice and brine once. The ethyl acetate layer was dried, filtered, and removed under reduced pressure, and the residual material was chromatographed using a 20-50% gradient of heptane/ethyl acetate to afford 3-{3,5-dimethyl-4-[6-(quinolin-2-ylcarbamoyl)-1H-indol-2-yl]-phenyl}-propionic acid methyl ester. 1H NMR (DMSO-d6, 400 MHz): δ 11.56 (s, 1H), 11.00 (s, 1H), 8.39 (s, 2H), 8.16 (s, 1H), 7.95 (d, J=7.4 Hz, 1H), 7.88 (d, J=8.3 Hz, 1H), 7.79 (dd, J=8.3, 1.5 Hz, 1H), 7.73 (TD, J=7.0, 1.4 Hz, 1H), 7.63 (d, J=8.3 Hz, 1H), 7.52 (t, J=7.0 Hz, 1H), 7.05 (s, 2H), 6.41 (d, J=1.3 Hz, 1H), 3.62 (s, 3H), 2.85 (t, J=7.4 Hz, 2H), 2.67 (t, J=7.4 Hz, 2H), 2.12 (s, 6H). MS (m/z) 478.2 (M+1); Retention time=1.58 min (Method 10).

後処理

  1. extractionextracted with water twice
  2. dry with materialThe ethyl acetate layer was dried
  3. filtrationfiltered
  4. customremoved under reduced pressure
  5. customthe residual material was chromatographed

出典と根拠

ORDレコード
ord-8b9f846e892f4cb9aad681cff2ea7e13
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08222248B2

反応ノート

読み込み中…

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