1-Hydroxybenzotriazole → 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(1-(pyridin-4-yl)ethyl)piperidine-4-carboxamide

HRID 83621

반응식

HRID 83621 반응식
Cl.C(N=C=NCCCN(C)C)C.[Cl:13][C:14]1[CH:40]=[CH:39][C:17]([CH2:18][N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[C:20]2[C:28]([N:30]2[CH2:35][CH2:34][CH:33]([C:36]([OH:38])=O)[CH2:32][CH2:31]2)=[O:29])=[CH:16][CH:15]=1.N1(O)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[N:60]1[CH:65]=[CH:64][C:63]([CH:66]([NH2:68])[CH3:67])=[CH:62][CH:61]=1>C(Cl)Cl.O.C(OCC)(=O)C>[Cl:13][C:14]1[CH:40]=[CH:39][C:17]([CH2:18][N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[C:20]2[C:28]([N:30]2[CH2:31][CH2:32][CH:33]([C:36]([NH:68][CH:66]([C:63]3[CH:64]=[CH:65][N:60]=[CH:61][CH:62]=3)[CH3:67])=[O:38])[CH2:34][CH2:35]2)=[O:29])=[CH:16][CH:15]=1

참가 물질

9

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2479981-(Pyridin-4-yl)ethan-1-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

생성물 1

HCID 665712181-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(1-(pyridin-4-yl)ethyl)piperidine-4-carboxamide

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (259 mg, 1.350 mmol), 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (428 mg, 1.080 mmol), and 1H-benzo[d][1,2,3]triazol-1-ol (182 mg, 1.350 mmol) were dissolved in 4.0 mL of DCM. The reaction was stirred at room temperature for ten minutes before Hunig's Base (0.236 ml, 1.350 mmol) and 1-(4-pyridinyl)ethanamine as a 1.0 mL DCM solution was added. The reaction was allowed to stir at room temperature overnight. The reaction was diluted with water and ethyl acetate. The organic phase was washed with water, saturated sodium bicarbonate (twice), and saturated sodium chloride. The organic phase was dried over magnesium sulfate, filtered and concentrated. The crude material was triturated with ether and ethyl acetate and filtered to obtain white solid as a product. (Yield: 37.9 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 8.52-8.45, 8.35, 7.62, 7.53, 7.36-7.30, 7.30-7.25, 7.24-7.18, 7.13-7.06, 6.72, 5.48, 4.87, 4.57-3.84, 2.93, 2.48-2.42, 1.71, 1.58-1.26

후처리

  1. additionwas added
  2. washThe organic phase was washed with water, saturated sodium bicarbonate (twice), and saturated sodium chloride
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was triturated with ether and ethyl acetate
  7. filtrationfiltered
  8. customto obtain white solid as a product

출처 및 근거

ORD 기록
ord-e35f976bcdf84046a82fef50b45aafb7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846684B2

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