Lawesson's reagent → HCID 178527718, compound

HRID 1710374Notes

Reaction equation

[C:1]1([C:7]2[CH:8]=[C:9]3[N:15]=[C:14]([CH2:16][CH2:17][CH:18]4[NH:24][C:23](=O)[CH2:22][CH2:21][CH2:20][CH2:19]4)[NH:13][C:10]3=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1>C1(C)C=CC=CC=1>[C:1]1([C:7]2[CH:8]=[C:9]3[N:15]=[C:14]([CH2:16][CH2:17][CH:18]4[NH:24][C:23](=[S:35])[CH2:22][CH2:21][CH2:20][CH2:19]4)[NH:13][C:10]3=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 100 °C

Procedure

90 mg of 7-[2-(6-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-azepan-2-one (compound B1) are dissolved in 10 ml of toluene under an atmosphere of dry nitrogen. Subsequently, 144 mg of Lawesson's reagent are added and the solution is heated at 100° C. for 17 hours. Thereafter, the reaction mixture is evaporated to dryness to yield approximately 200 mg of crude material, which is purified by chromatography on basic aluminum oxide (eluent: dichloromethane) to afford 71 mg of the title compound as a light yellow, waxy solid. ESI-MS: 351.2 (MH+). TLC: Rf=0.53 (dichloromethane/ethanol 10:1 parts by volume).

Workup

customThereafter, the reaction mixture is evaporated to dryness
customto yield approximately 200 mg of crude material, which
customis purified by chromatography on basic aluminum oxide (eluent: dichloromethane)

Sources & evidence

ORD record: ord-4b1be3494c0d4e5c8e213bc2967a5241
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790710B2

Reaction notes

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