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

HRID 1710379Notes

Reaction equation

HRID 1710379 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[C:21]3[N:27]=[C:26]([CH2:28][CH2:29][CH:30]4[CH2:36][CH2:35][CH2:34][CH2:33][C:32](=O)[NH:31]4)[NH:25][C:22]3=[N:23][CH:24]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:47])=CC=1>O1CCOCC1>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[C:21]3[N:27]=[C:26]([CH2:28][CH2:29][CH:30]4[CH2:36][CH2:35][CH2:34][CH2:33][C:32](=[S:47])[NH:31]4)[NH:25][C:22]3=[N:23][CH:24]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 178426725N-(2-fluoro-4-methyl-phenyl)-4-{2-[2-(7-oxo-azepan-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-benzenesulfonamide2×

Product 1

HCID 178426726N-(2-fluoro-4-methyl-phenyl)-4-{2-[2-(7-thioxo-azepan-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-benzenesulfonamideYield 57.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title compound is analogously 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 180 mg of N-(2-fluoro-4-methyl-phenyl)-4-{2-[2-(7-oxo-azepan-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-benzenesulfonamide (compound B8) and 146 mg of Lawesson's reagent at 100° C. for 3 hours in 20 ml of dioxane. Purification by chromatography on flash silica gel (eluent gradient: dichloromethane/0-10 vol. % ethanol) affords 106 mg of the title compound as a colorless solid of m.p. 271° C. ESI-MS: 538.2 (MH+). TLC: Rf=0.40 (dichloromethane/ethanol 10:1 parts by volume).

Workup

  1. customPurification by chromatography on flash silica gel (eluent gradient: dichloromethane/0-10 vol. % ethanol)

Sources & evidence

ORD record
ord-2b763e6cfa7c435ca32f53d519283ba0
Source dataset
uspto-grants-2010_09
Patent number
US07790710B2

Reaction notes

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