Lawesson's reagent → N,N-dimethyl-4-{2-[2-(7-thioxo-azepan-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-benzenesulfonamide

HRID 1710376

Reaktionsgleichung

Reaktionsgleichung von HRID 1710376
[CH3:1][N:2]([CH3:31])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[N:20]=[C:19]([CH2:21][CH2:22][CH:23]4[CH2:29][CH2:28][CH2:27][CH2:26][C:25](=O)[NH:24]4)[NH:18][C:15]3=[N:16][CH:17]=2)=[CH:8][CH:7]=1)(=[O:5])=[O:4].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:41])=CC=1>>[CH3:1][N:2]([CH3:31])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[N:20]=[C:19]([CH2:21][CH2:22][CH:23]4[CH2:29][CH2:28][CH2:27][CH2:26][C:25](=[S:41])[NH:24]4)[NH:18][C:15]3=[N:16][CH:17]=2)=[CH:8][CH:7]=1)(=[O:5])=[O:4]

Komponenten

3

Edukt 2

HCID 87949Lawesson's reagentHCID 178486133HCID 178486133, Verbindung2×

Produkt 1

HCID 178486134N,N-dimethyl-4-{2-[2-(7-thioxo-azepan-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-benzenesulfonamideAusbeute 63,6 %

Versuchsvorschrift

The title compound is synthesized as described for 7-[2-(6-{4-cyano-phen-1-yl}-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-azepan-2-thione (compound A2) from 85 mg of N,N-dimethyl-4-{2-[2-(7-oxo-azepan-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-benzenesulfonamide (compound B5) and 82 mg of Lawesson's reagent. Purification by chromatography on flash silica gel (eluent gradient: dichloromethane/0-5 vol. % ethanol) affords 56 mg of the title compound as a light yellow, waxy solid. ESI-MS: 458.3 (MH+). TLC: Rf=0.46 (dichloromethane/ethanol 10:1 parts by volume).

Aufarbeitung

  1. customThe title compound is synthesized
  2. customPurification by chromatography on flash silica gel (eluent gradient: dichloromethane/0-5 vol. % ethanol)

Quellen und Nachweise

ORD-Eintrag
ord-8879062418b44025be2bba03ec59f44f
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790710B2

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