Dichloromethane → N-(2-thienylmethyl)-2-[2-[3-(trifluoromethyl)-phenyl]sulfonylethylthio]-3-quinoline carboxamide

HRID 1949171Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].Cl[CH2:8][CH2:9][S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)(=[O:12])=[O:11].[SH:23][C:24]1[C:33]([C:34]([NH:36][CH2:37][C:38]2[S:39][CH:40]=[CH:41][CH:42]=2)=[O:35])=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=1.C(Cl)Cl>CC(C)=O>[S:39]1[CH:40]=[CH:41][CH:42]=[C:38]1[CH2:37][NH:36][C:34]([C:33]1[C:24]([S:23][CH2:8][CH2:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)(=[O:12])=[O:11])=[N:25][C:26]2[C:31]([CH:32]=1)=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:35]

Participants

Conditions

Temperature: 70 °C

Procedure

151 mg (1.1 mmol) K2CO3 and 300 mg (1.1 mmol) 1-(2-chloroethylsulfonyl)-3-(trifluoromethyl)benzene were added to a solution of 300 mg (1.0 mmol) 2-mercapto-N-(thiophen-2-ylmethyl)quinoline-3-carboxamide (precursor VVV02) in acetone (10 ml) at RT and the mixture was heated for 3 h at 70° C. Then it was filtered and the filtrate was concentrated to small volume under vacuum. The residue was taken up with EE and washed with water and brine, dried over MgSO4, filtered and concentrated to small volume under vacuum. Column chromatography (DCM/EE 20:1) of the residue yielded 163 mg (0.3 mmol, 30%) N-(2-thienylmethyl)-2-[2-[3-(trifluoromethyl)-phenyl]sulfonylethylthio]-3-quinoline carboxamide. MS: m/z 537.1 [M+H]+.

Workup

filtrationThen it was filtered
concentrationthe filtrate was concentrated to small volume under vacuum
washwashed with water and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record: ord-b12696f819e043679217a6db1f51d0f6
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399673B2

Reaction notes

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