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Dimethylformamide → 5-[[1-[1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]-1,2,3,4-tetrahydro-6-quinolinyl]oxy]-N-propylpentanamide

HRID 585377
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 585377
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:37]=[CH:38][C:39]=1[O:40][CH3:41])[C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]([N:18]2[C:27]3[C:22](=[CH:23][C:24]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33](O)=[O:34])=[CH:25][CH:26]=3)[CH2:21][CH2:20][CH2:19]2)[CH2:10][CH:9]1[CH3:36])=[O:7].C(Cl)(=O)C(Cl)=O.CN(C=O)C.[CH2:53]([NH2:56])[CH2:54][CH3:55]>C1COCC1.N1C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:37]=[CH:38][C:39]=1[O:40][CH3:41])[C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]([N:18]2[C:27]3[C:22](=[CH:23][C:24]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([NH:56][CH2:53][CH2:54][CH3:55])=[O:34])=[CH:25][CH:26]=3)[CH2:21][CH2:20][CH2:19]2)[CH2:10][CH:9]1[CH3:36])=[O:7]
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Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 7852PropylamineHCID 65578Oxalyl chlorideHCID 223392615-[[1-[1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]-1,2,3,4-tetrahydro-6-quinolinyl]oxy]pentanoic aicd

Produkt 1

HCID 223392235-[[1-[1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]-1,2,3,4-tetrahydro-6-quinolinyl]oxy]-N-propylpentanamide
Ausbeute 24,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-[[1-[1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]-1,2,3,4-tetrahydro-6-quinolinyl]oxy]pentanoic acid (197 mg, 0.35 mmol) prepared in Example 95 was dissolved in THF (10 ml), to which oxalyl chloride (0.079 ml, 1.05 mmol) and DMF (0.1 ml) were then added on ice and stirred at room temperature for 1 hour. After the reaction mixture was concentrated, the residue was dissolved in pyridine (10 ml) on ice and propylamine (62 mg, 1.05 mmol) was added thereto, followed by stirring at room temperature for 16 hours. After the reaction mixture was diluted with ethyl acetate, washed with water, dried and concentrated, the residue was applied to silica gel column chromatography (developing solvent: ethyl acetate/hexane=4/1) to give the titled compound (51 mg, yield: 24%) as a colorless oil. (cis:trans=1:2.8)

Aufarbeitung

  1. additionwere then added on ice
  2. concentrationAfter the reaction mixture was concentrated
  3. additionwas added
  4. stirringby stirring at room temperature for 16 hours
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e625e1f657334c31a4c9049b8dc82dee
Quelldatensatz
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06930104B2

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