Water → 5-{[2-([Ethylsulfanyl]methyl)-1-(2-fluoro-4-methoxyphenyl)-3,3,3-trifluoro-2-hydroxypropyl]amino}-1H-quinolin-2-one

HRID 1945103Notes

Reaction equation

HRID 1945103 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]([NH:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH:21]=[CH:22][C:23](=[O:29])[NH:24]2)[C:11]1([C:14]([F:17])([F:16])[F:15])[CH2:13][O:12]1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:36]([SH:38])[CH3:37].O>CN(C=O)C>[CH2:36]([S:38][CH2:13][C:11]([OH:12])([C:14]([F:16])([F:15])[F:17])[CH:10]([NH:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH:21]=[CH:22][C:23](=[O:29])[NH:24]2)[C:3]1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=1[F:1])[CH3:37]

Participants

6

Reactant 4

HCID 962WaterHCID 6343EthanethiolHCID 10796Cesium carbonateHCID 866305555-{[(2-Fluoro-4-methoxyphenyl)(2-trifluoromethyl-oxiranyl)methyl]amino}-1H-quinolin-2-one

Product 1

HCID 426231885-{[2-([Ethylsulfanyl]methyl)-1-(2-fluoro-4-methoxyphenyl)-3,3,3-trifluoro-2-hydroxypropyl]amino}-1H-quinolin-2-oneYield 35.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 50 mg (0.12 mmol) 5-{[(2-Fluoro-4-methoxyphenyl)(2-trifluoromethyl-oxiranyl)methyl]amino}-1H-quinolin-2-one and 80 mg Cs2CO3 in 0.5 ml DMF are added 14 μl (0.18 mmol) of ethyl mercaptan in DMF. The mixture is stirred vigorously for 4 hours and water is added. The aqueous layer is extracted with ethyl acetate, the organic phases washed with brine and dried over sodium sulphate. After removal of the solvent thin layer chromatography on silica gel (acetone in hexane 50%) yields 20 mg of the title compound.

Workup

  1. extractionThe aqueous layer is extracted with ethyl acetate
  2. washthe organic phases washed with brine
  3. dry with materialdried over sodium sulphate
  4. customAfter removal of the solvent thin layer chromatography on silica gel (acetone in hexane 50%)

Sources & evidence

ORD record
ord-425b8c4f5ba34736be839f04fae6aa77
Source dataset
uspto-grants-2013_03
Patent number
US08394958B2

Reaction notes

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