Lawesson's reagent → HCID 178462789, compound

HRID 1710378Notes

Reaction equation

HRID 1710378 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[C:20]4[N:26]=[C:25]([CH2:27][CH2:28][CH:29]5[NH:35][C:34](=O)[CH2:33][CH2:32][CH2:31][CH2:30]5)[NH:24][C:21]4=[N:22][CH:23]=3)=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH2:5][CH2:4]1)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:46])=CC=1>O1CCOCC1>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[C:20]4[N:26]=[C:25]([CH2:27][CH2:28][CH:29]5[NH:35][C:34](=[S:46])[CH2:33][CH2:32][CH2:31][CH2:30]5)[NH:24][C:21]4=[N:22][CH:23]=3)=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH2:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 178462788HCID 178462788, compound2×

Product 1

HCID 178462789HCID 178462789, compoundYield 93%

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 170 mg of 7-(2-{6-[4-(4-ethyl-piperazine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl}-ethyl)-azepan-2-one (compound B7) and 142 mg of Lawesson's reagent at 100° C. for 2.5 hours in 20 ml of dioxane. Purification by chromatography on flash silica gel (eluent gradient: dichloromethane/0-10 vol. % ethanol) affords 163 mg of the title compound as a waxy solid. ESI-MS: 527.3 (MH+). TLC: Rf=0.34 (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-7a768860cb7849a98279251b2e18d81e
Source dataset
uspto-grants-2010_09
Patent number
US07790710B2

Reaction notes

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