Lawesson's reagent → HCID 178424388, compound

HRID 1710380Notes

Reaction equation

O=[C:2]1[NH:8][CH:7]([CH2:9][CH2:10][C:11]2[NH:36][C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([S:25]([NH:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=5[CH3:35])(=[O:27])=[O:26])=[CH:21][CH:20]=4)[CH:18]=[C:13]3[N:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:46])=CC=1>>[S:46]=[C:2]1[NH:8][CH:7]([CH2:9][CH2:10][C:11]2[NH:36][C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([S:25]([NH:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=5[CH3:35])(=[O:27])=[O:26])=[CH:21][CH:20]=4)[CH:18]=[C:13]3[N:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

Reactant 2

HCID 87949Lawesson's reagent

HCID 178424387HCID 178424387, compound2×

Product 1

HCID 178424388HCID 178424388, compoundYield 85.9%

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 88 mg of 4-{2-[2-(7-oxo-azepan-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-N-o-tolyl-benzenesulfonamide (compound B9) and 77 mg of Lawesson's reagent. Purification by chromatography on LiChroprep-NH2® (eluents: i. neat dichloromethane, ii. dichloromethane/ethanol 20:1 parts by volume) affords 78 mg of the title compound as a waxy solid. ESI-MS: 520.4 (MH+). TLC: Rf=0.44 (LiChroprep-NH2® HPTLC, dichloromethane/ethanol 10:1 parts by volume).

Workup

customPurification by chromatography on LiChroprep-NH2® (eluents: i. neat dichloromethane, ii. dichloromethane/ethanol 20:1 parts by volume)

Sources & evidence

ORD record: ord-8a3a4b29e8b44365b810f52664b45ef1
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790710B2

Reaction notes

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