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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
Notes
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Reaction equation

HRID 1514957 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8b9f846e892f4cb9aad681cff2ea7e13
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08222248B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes