Dimethylamine → HCID 59486213, compound

HRID 1949177Notes

Reaction equation

HRID 1949177 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][NH:8][CH3:9].Cl[C:11]1[C:20]2[C:15](=[CH:16][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:18][CH:19]=2)[N:14]=[C:13]([S:25][CH2:26][CH3:27])[C:12]=1[C:28]([NH:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=1)=[O:29].CCCCCC>CN(C=O)C.O>[CH3:7][N:8]([CH3:9])[C:11]1[C:20]2[C:15](=[CH:16][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:18][CH:19]=2)[N:14]=[C:13]([S:25][CH2:26][CH3:27])[C:12]=1[C:28]([NH:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=1)=[O:29]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8058HexaneHCID 11430Potassium CarbonateHCID 59486210HCID 59486210, compound

Product 1

HCID 59486213HCID 59486213, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

60 mg (0.45 mmol) K2CO3 and 0.7 ml (1.36 mmol, 2M in THF) dimethylamine were added at RT to a solution of 200 mg (0.45 mmol) 4-chloro-2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-7-(trifluoromethyl)-quinoline-3-carboxamide (example 122) in DMF (3 ml) and the mixture was then heated in a closed vessel for 150 min at 80°. Then it was diluted with water and extracted with EE. The organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 17:3) of the residue yielded 120 mg (0.27 mmol, 60%) 4-dimethylamino-2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-7-(trifluoromethyl)-quinoline-3-carboxamide. MS: m/z 452.1 [M+H]+.

Workup

  1. temperaturethe mixture was then heated in a closed vessel for 150 min at 80°
  2. extractionextracted with EE
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-54aa6a3d681244bdadba331d55191a1c
Source dataset
uspto-grants-2013_03
Patent number
US08399673B2

Reaction notes

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