1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-((1-methylpiperidin-4-yl)methyl)piperidine-4-carboxamide

HRID 83626

反応式

HRID 83626 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.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.[CH3:50][N:51]1[CH2:56][CH2:55][CH:54]([CH2:57][NH2:58])[CH2:53][CH2:52]1>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[CH2:23][CH2:22][CH:21]([C:24]([NH:58][CH2:57][CH:54]3[CH2:55][CH2:56][N:51]([CH3:50])[CH2:52][CH2:53]3)=[O:26])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 815741-Methylpiperidine-4-methylamineHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

生成物 1

HCID 665713371-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-((1-methylpiperidin-4-yl)methyl)piperidine-4-carboxamide

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-hydroxybenzotriazole (68.1 mg, 0.504 mmol) and EDCI (97 mg, 0.504 mmol) were dissolved in DCM (Volume: 4.0 ml). The suspension was stirred at room temperature for 10 minutes where it turned clear. Hunig'sBase (0.132 ml, 0.756 mmol) and (1-methylpiperidin-4-yl)methanamine (100 mg, 0.780 mmol) were added. The reaction was stirred at room temperature overnight. It was diluted with water and ethyl acetate. The water layer was washed with another portion of ethyl acetate. The combined organic layer was washed with saturated sodium bicarbonate and saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The resulting crude material was triturated with diethyl ether/ethyl acetate to afford the product as a white solid. (Yield: 83 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 7.77, 7.62, 7.54, 7.35-7.30, 7.21, 7.13-7.06, 6.72, 5.49, 4.38, 4.02, 2.93, 2.78, 2.42-2.30, 2.17, 1.77, 1.57, 1.45-1.02

後処理

  1. stirringThe reaction was stirred at room temperature overnight
  2. washThe water layer was washed with another portion of ethyl acetate
  3. washThe combined organic layer was washed with saturated sodium bicarbonate and saturated sodium chloride
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting crude material was triturated with diethyl ether/ethyl acetate

出典と根拠

ORDレコード
ord-ca4064e8103c40daac5d45239499cdb1
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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