N-Methylbenzylamine → N-benzyl-1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide

HRID 83605

反応式

HRID 83605 の反応式
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24](O)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[CH3:59][NH:60][CH2:61][C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1>C(Cl)Cl.O.C(OCC)(=O)C>[CH2:61]([N:60]([CH3:59])[C:24]([CH:21]1[CH2:22][CH2:23][N:18]([C:16]([C:8]2[N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:28][CH:27]=3)[C:15]3[C:10]([CH:9]=2)=[CH:11][CH:12]=[CH:13][CH:14]=3)=[O:17])[CH2:19][CH2:20]1)=[O:25])[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1

参加物

9

反応物 5

HCID 7669N-MethylbenzylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

生成物 1

HCID 66571095N-benzyl-1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (150 mg, 0.378 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (145 mg, 0.756 mmol), and 1-Hydroxybenzotriazole (102 mg, 0.756 mmol) were dissolved in 2.0 mL of DCM. The reaction was allowed to stir for 10 minutes before N,N-Diisopropylethylamine (132 μL, 0.756 mmol) and N-methyl-1-phenylmethanamine (45.8 mg, 0.378 mmol) were added as a 1.0 mL DCM solution. The reaction was allowed to stir overnight. The reaction was diluted with water and ethyl acetate. The layers were separated and the organic layer was washed with another aliquot of water. The ethyl acetate layer was washed with 1N HCl followed by saturated sodium bicarbonate then saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude material was triturated with methanol and filtered under vacuum to obtain pure product as a white solid. Yield: 63.7 mg (White solid)

後処理

  1. customThe layers were separated
  2. washthe organic layer was washed with another aliquot of water
  3. washThe ethyl acetate layer was washed with 1N HCl
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was triturated with methanol
  8. filtrationfiltered under vacuum
  9. customto obtain pure product as a white solid

出典と根拠

ORDレコード
ord-c8c8a21661a646478d543c99802c78ca
出典データセット
uspto-grants-2014_09
特許番号
US08846684B2

関連ノート

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