Propyl mercaptan → HCID 59486214, compound

HRID 1949173Notes

Reaction equation

HRID 1949173 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7]([SH:10])[CH2:8][CH3:9].Cl[C:12]1[C:21]([C:22]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=2)=[O:23])=[C:20]([CH3:33])[C:19]2[C:14](=[CH:15][C:16]([C:34]([F:37])([F:36])[F:35])=[CH:17][CH:18]=2)[N:13]=1.CCCCCC>CN(C=O)C.O>[F:32][C:28]1[CH:27]=[C:26]([CH2:25][NH:24][C:22]([C:21]2[C:12]([S:10][CH2:7][CH2:8][CH3:9])=[N:13][C:14]3[C:19]([C:20]=2[CH3:33])=[CH:18][CH:17]=[C:16]([C:34]([F:37])([F:36])[F:35])[CH:15]=3)=[O:23])[CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 7848Propyl mercaptanHCID 8058HexaneHCID 11430Potassium CarbonateHCID 86645341HCID 86645341, compound

Product 1

HCID 59486214HCID 59486214, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

209 mg (1.5 mmol) K2CO3 and 137 μl (1.5 mmol) propanethiol were added to a solution of 200 mg (0.5 mmol) 2-chloro-N-[(3-fluorophenyl)-methyl]-4-methyl-7-(trifluoromethyl)-quinoline-3-carboxamide (VVV17) in DMF (4 ml) and the mixture was heated in a closed vessel for 72 h at 40° C. After cooling to RT the mixture was diluted with water and extracted with EE. The organic phase was washed with water and brine, dried over MgSO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 3:1) of the residue yielded 146 mg (0.33 mmol, 67%) N-[(3-fluorophenyl)-methyl]-4-methyl-2-(propylsulfanyl)-7-(trifluoromethyl)-quinoline-3-carboxamide. MS: m/z 437.1 [M+H]+.

Workup

  1. temperatureAfter cooling to RT the mixture
  2. extractionextracted with EE
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-d85a4f9ecb3b42cfa72978dd06bd2162
Source dataset
uspto-grants-2013_03
Patent number
US08399673B2

Reaction notes

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