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

HRID 83618
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 83618
Cl.C(N=C=NCCCN(C)C)C.N1(O)C2C=CC=CC=2N=N1.[Cl:23][C:24]1[CH:50]=[CH:49][C:27]([CH2:28][N:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=[C:30]2[C:38]([N:40]2[CH2:45][CH2:44][CH:43]([C:46]([OH:48])=O)[CH2:42][CH2:41]2)=[O:39])=[CH:26][CH:25]=1.C(N(C(C)C)C(C)C)C.[N:60]1[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=1[CH2:66][CH2:67][NH2:68]>C(Cl)Cl.O.C(OCC)(=O)C>[Cl:23][C:24]1[CH:50]=[CH:49][C:27]([CH2:28][N:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=[C:30]2[C:38]([N:40]2[CH2:45][CH2:44][CH:43]([C:46]([NH:68][CH2:67][CH2:66][C:61]3[CH:62]=[CH:63][CH:64]=[CH:65][N:60]=3)=[O:48])[CH2:42][CH2:41]2)=[O:39])=[CH:26][CH:25]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 759192-PyridineethanamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

Produkt 1

HCID 66571276
1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(2-(pyridin-2-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 (235 mg, 1.228 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (166 mg, 1.228 mmol), and 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (390 mg, 0.982 mmol) were dissolved in 4.0 mL of DCM. The reaction was stirred for ten minutes before adding N-ethyl-N-isopropylpropan-2-amine (0.214 ml, 1.228 mmol) and 2-(pyridin-2-yl)ethanamine (100 mg, 0.819 mmol) as a 1.0 mL DCM solution. The reaction was stirred overnight at room temperature. It 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. 1H-NMR (400 MHz, DMSO-d6) 8.46, 7.84, 7.66, 7.60, 7.51, 7.37-7.27, 7.24-7.14, 7.12-7.03, 6.69, 5.46, 4.58-3.75, 3.37, 3.12-2.67, 2.34-2.25, 1.59, 1.33

Aufarbeitung

  1. stirringThe reaction was stirred overnight at room temperature
  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-ca1b81ceb127419fb23845b8dcf45c21
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846684B2

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