1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (1-(4-chlorobenzyl)-1H-indol-2-yl)(4-(pyrrolidine-1-carbonyl)piperidin-1-yl)methanone

HRID 83598

反応式

HRID 83598 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]([OH:26])=O)[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1.C(N=C=N[CH2:34][CH2:35][CH2:36][N:37]([CH3:39])C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.N1CCCC1>C(Cl)Cl.O.C(OCC)(=O)C>[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[CH2:19][CH2:20][CH:21]([C:24]([N:37]3[CH2:36][CH2:35][CH2:34][CH2:39]3)=[O:26])[CH2:22][CH2:23]2)=[O:17])=[CH:4][CH:3]=1

参加物

9

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

生成物 1

HCID 66571094(1-(4-chlorobenzyl)-1H-indol-2-yl)(4-(pyrrolidine-1-carbonyl)piperidin-1-yl)methanone

試薬・触媒・溶媒 3

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

実験手順

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (100 mg, 0.252 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (97 mg, 0.504 mmol), and 1-Hydroxybenzotriazole (68 mg, 0.504 mmol) were dissolved in 3.0 mL of DCM. The reaction was allowed to stir for 10 minutes before N,N-Diisopropylethylamine (88 μL, 0.504 mmol) and pyrrolidine (41.7 μL, 0.504 mmol) were added. 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 saturated citric acid, saturated sodium bicarbonate, and saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude material was purified in silica gel using the gradient 100% DCM to 5% 7M NH3 in methanol diluted with 95% DCM. After purification, pure white solid was obtained. Yield: 83 mg (White solid)

後処理

  1. additionwere added
  2. customThe layers were separated
  3. washthe organic layer was washed with another aliquot of water
  4. washThe ethyl acetate layer was washed with saturated citric acid, saturated sodium bicarbonate, and saturated sodium chloride
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified in silica gel using the gradient 100% DCM to 5% 7M NH3 in methanol
  9. additiondiluted with 95% DCM
  10. customAfter purification
  11. custompure white solid was obtained

出典と根拠

ORDレコード
ord-084db5713a304a009af2ee7c6d8438d6
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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