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

HRID 83621

Reaktionsgleichung

Reaktionsgleichung von HRID 83621
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

Komponenten

9

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e35f976bcdf84046a82fef50b45aafb7
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846684B2

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