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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
Notes
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Reaction equation

HRID 585377 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 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

Product 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
Yield 24.3%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-e625e1f657334c31a4c9049b8dc82dee
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06930104B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes