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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
ノート
印刷プレビュー

反応式

HRID 585377 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 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
収率 24.3%

試薬・触媒・溶媒 3

HCID 1049Pyridine溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-e625e1f657334c31a4c9049b8dc82dee
出典データセット
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06930104B2

反応ノート

読み込み中…

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