1-Hydroxybenzotriazole → 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-((1-methyl-1H-pyrazol-3-yl)methyl)piperidine-4-carboxamide

HRID 83628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 83628
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](O)=[O:37])[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.[CH3:60][N:61]1[CH:65]=[CH:64][C:63]([CH2:66][NH2:67])=[N:62]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:67][CH2:66][C:63]3[CH:64]=[CH:65][N:61]([CH3:60])[N:62]=3)=[O:37])[CH2:34][CH2:35]2)=[O:29])=[CH:16][CH:15]=1

Komponenten

9

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7019419(1-Methylpyrazol-3-yl)methanamineHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

Produkt 1

HCID 665713351-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-((1-methyl-1H-pyrazol-3-yl)methyl)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-methyl-1H-pyrazol-3-yl)methanamine (100 mg, 0.900 mmol) 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 layer was washed with water, saturated sodium bicarbonate (twice), and saturated sodium chloride. The organic phase was dried over magnesium sulfate, filtered and concentrated. The resulting material was triturated with ethyl acetate to obtain white solid as the product. 1H-NMR (400 MHz, DMSO-d6) 8.18, 7.66-7.51, 7.35, 7.22, 7.12, 6.73, 6.05, 5.49, 4.40, 4.18, 3.96, 3.77, 2.93, 2.41, 1.69, 1.44

Aufarbeitung

  1. additionwas added
  2. washThe organic layer 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 resulting material was triturated with ethyl acetate
  7. customto obtain white solid as the product

Quellen und Nachweise

ORD-Eintrag
ord-1a9f9eb6fb2849dc891c2361a2c2c9a7
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846684B2

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