Lawesson's reagent → HCID 178482880, compound

HRID 1710381Notes

Reaction equation

HRID 1710381 reaction equation
[CH3:1][N:2]([CH2:31][CH:32]1[CH2:36][CH2:35][CH2:34][O:33]1)[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:46])=CC=1>>[CH3:1][N:2]([CH2:31][CH:32]1[CH2:36][CH2:35][CH2:34][O:33]1)[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:46])[NH:24]4)[NH:18][C:15]3=[N:16][CH:17]=2)=[CH:8][CH:7]=1)(=[O:5])=[O:4]

Participants

3

Reactant 2

HCID 87949Lawesson's reagentHCID 178482879HCID 178482879, compound

Product 1

HCID 178482880HCID 178482880, compoundYield 95.4%

Procedure

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 125 mg of N-methyl-4-{2-[2-(7-oxo-azepan-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-N-(tetrahydro-furan-2-ylmethyl)-benzenesulfonamide (compound B10) and 104 mg of Lawesson's reagent. Purification by chromatography on flash silica gel (eluent gradient: dichloromethane/0-10 vol. % ethanol) affords 123 mg of the title compound as a waxy solid. ESI-MS: 528.9 (MH+). TLC: Rf=0.43 (dichloromethane/ethanol 10:1 parts by volume).

Workup

  1. customThe title compound is synthesized
  2. customPurification by chromatography on flash silica gel (eluent gradient: dichloromethane/0-10 vol. % ethanol)

Sources & evidence

ORD record
ord-136c488b0abc42d18213055187795a24
Source dataset
uspto-grants-2010_09
Patent number
US07790710B2

Reaction notes

Loading…