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1,2-Dichloroethane → 1-(1-(4-chlorobenzyl)-1H-benzo[d]imidazole-2-carbonyl)-N-(2-(pyridin-4-yl)ethyl)piperidine-4-carboxamide

HRID 83653
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HRID 83653 반응식
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N: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(Cl)CCl.ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[N:52]1[CH:57]=[CH:56][C:55]([CH2:58][CH2:59][NH2:60])=[CH:54][CH:53]=1>C(Cl)Cl.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([NH:60][CH2:59][CH2:58][C:55]3[CH:56]=[CH:57][N:52]=[CH:53][CH:54]=3)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:27][CH:28]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 832754-PyridineethanamineHCID 683800451-(1-(4-chlorobenzyl)-1H-benzo[d]imidazole-2-carbonyl)piperidine-4-carboxylic acid

생성물 1

HCID 66571519
1-(1-(4-chlorobenzyl)-1H-benzo[d]imidazole-2-carbonyl)-N-(2-(pyridin-4-yl)ethyl)piperidine-4-carboxamide

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

1-(1-(4-chlorobenzyl)-1H-benzo[d]imidazole-2-carbonyl)piperidine-4-carboxylic acid (50 mg, 0.126 mmol), EDC (48.2 mg, 0.251 mmol), and 1-hydroxybenzotriazole (34.0 mg, 0.251 mmol) were dissolved in DCM (Volume: 2.0 mL). The reaction was allowed to stir for 10 minutes before the addition of Hunig's Base (0.044 mL, 0.251 mmol) and 2-(pyridin-4-yl)ethanamine (0.030 mL, 0.251 mmol). The reaction was allowed to stir overnight. The reaction was diluted with water and ethyl acetate. The organic layer was washed with saturated sodium bicarbonate and saturated sodium chloride. The ethyl acetate layer was dried over magnesium sulfate, filtered and concentrated. The crude material was triturated in diethyl ether/ethyl acetate to obtain white solid. 1H-NMR (500 MHz, DMSO-d6) 8.47-8.43, 7.93, 7.74, 7.61, 7.39, 7.35-7.24, 7.21, 5.55, 4.45, 3.98, 3.33-3.28, 3.04, 2.87, 2.73, 2.40-2.31, 1.74, 1.58-1.32

후처리

  1. washThe organic layer was washed with saturated sodium bicarbonate and saturated sodium chloride
  2. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was triturated in diethyl ether/ethyl acetate
  6. customto obtain white solid

출처 및 근거

ORD 기록
ord-9b19dee1017449189f94044d46d2e729
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846684B2

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