1-Hydroxybenzotriazole → 7-{[(5-Chloro-2-thienyl)sulfonyl]amino}-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide

HRID 1851450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1851450
[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:19]=2[NH:18][C:17]([C:20](O)=[O:21])=[CH:16]3)(=[O:9])=[O:8])=[CH:4][CH:3]=1.Cl.[C:24]([S:43][CH2:44][CH2:45][NH2:46])([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>O.CN(C)C=O.C(N(CC)CC)C>[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:19]=2[NH:18][C:17]([C:20]([NH:46][CH2:45][CH2:44][S:43][C:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:21])=[CH:16]3)(=[O:8])=[O:9])=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184272672-(Tritylthio)ethylamine hydrochlorideHCID 579018287-{[(5-Chloro-2-thienyl)sulfonyl]amino}-1H-indole-2-carboxylic acid

Produkt 1

HCID 579017477-{[(5-Chloro-2-thienyl)sulfonyl]amino}-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamideAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a mixture of 7-{[(5-chloro-2-thienyl)sulfonyl]amino}-1H-indole-2-carboxylic acid (0.84 g), 2-(tritylthio)ethylamine hydrochloride (0.85 g), 1H-1,2,3-benzotriazol-1-ol (0.35 g), triethylamine (0.36 mL) and N,N-dimethylformamide (20 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.50 g) at 0° C., and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the obtained crystals were filtrated, washed with water and dried. The obtained crystals were subjected to silica gel column chromatography and the title compound (1.41 g, yield 97%) was obtained as colorless crystals from a fraction eluted with ethyl acetate. melting point>197° C. (decomposition).

Aufarbeitung

  1. filtrationthe obtained crystals were filtrated
  2. washwashed with water
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ad02b18ea112423cbe005fbae01f741e
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957070B2

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