1-Hydroxybenzotriazole → N-[3-(2,3-dimethyl-3H-imidazol-4-yl)-phenyl]-9H-carbazole-1-carboxamide

HRID 1835437Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1835437
[C:1]1([C:14]([OH:16])=O)[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH3:39][N:40]1[C:44]([C:45]2[CH:46]=[C:47]([CH:49]=[CH:50][CH:51]=2)[NH2:48])=[CH:43][N:42]=[C:41]1[CH3:52]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:52][C:41]1[N:40]([CH3:39])[C:44]([C:45]2[CH:46]=[C:47]([NH:48][C:14]([C:1]3[C:13]4[NH:12][C:11]5[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=5)[C:5]=4[CH:4]=[CH:3][CH:2]=3)=[O:16])[CH:49]=[CH:50][CH:51]=2)=[CH:43][N:42]=1

Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 2389249h-Carbazole-1-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 235036623-(1,2-dimethyl-1H-imidazol-5-yl)aniline

Produkt 1

HCID 23503652N-[3-(2,3-dimethyl-3H-imidazol-4-yl)-phenyl]-9H-carbazole-1-carboxamideAusbeute 53,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 9H-carbazole-1-carboxylic acid (106 mg) and 1-hydroxybenzotriazole (81 mg) in dichloromethane (2 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (144 mg) and the mixture was stirred for 15 minutes. After adding 3-(1,2-dimethylimidazol-5-yl)aniline (94 mg) and 4-dimethylaminopyridine (92 mg), the mixture was stirred for 60 hours. The residue was evaporated under reduced pressure and purified by a silica gel column chromatography eluting with 2% methanol in dichloromethane to give N-[3-(2,3-dimethyl-3H-imidazol-4-yl)-phenyl]-9H-carbazole-1-carboxamide (101 mg, 53.2%).

Aufarbeitung

  1. stirringthe mixture was stirred for 60 hours
  2. customThe residue was evaporated under reduced pressure
  3. custompurified by a silica gel column chromatography
  4. washeluting with 2% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-84c55895af574d03bbf808bb5896d99d
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06770667B1

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