Hexane → HCID 21072795, compound

HRID 1372887Notes

Reaction equation

HRID 1372887 reaction equation
[C:1]([NH:5][C:6](=[O:22])[C:7]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[CH3:20])=[CH:11][C:10](Cl)=[N:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[NH:23]1[CH2:28][CH2:27][S:26][CH2:25][CH2:24]1.CCCCCC>CS(C)=O.C(=O)([O-])[O-].[K+].[K+]>[C:1]([NH:5][C:6](=[O:22])[C:7]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[CH3:20])=[CH:11][C:10]([N:23]2[CH2:28][CH2:27][S:26][CH2:25][CH2:24]2)=[N:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8058HexaneHCID 67164ThiomorpholineHCID 11551512HCID 11551512, compound

Product 1

HCID 21072795HCID 21072795, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 11430Potassium CarbonateSolvent

Procedure

N-tert-Butyl-4-(4-fluoro-2-methyl-phenyl)-6-thiomorpholin-4-yl-nicotinamide can be then produced by dissolving N-tert-Butyl-6-chloro-4-(4-fluoro-2-methyl-phenyl)-nicotinamide in dimethylsulfoxide and potassium carbonate, followed by the addition of thiomorpholine. The resulting suspension is stirred, cooled to room temperature, and partitioned between ethyl acetate and half-saturated aqueous sodium chloride solution. The phases are then separated and the organic phase washed with half-saturated aqueous sodium chloride. The aqueous phases are then extracted with ethyl acetate. The combined organic extracts are dried and concentrated in a rotary evaporator to produce a yellow oil. This oil is heated with the dropwise addition of n-hexane to obtain a refluxing suspension, which can be cooled to room temperature and further stirred at 0° C. for about one hour. The precipitate is filtered off, washed with cold n-hexane:ethyl acetate 9:1, and dried in a vacuum oven to yield N-tert-butyl-4-(4-fluoro-2-methyl-phenyl)-6-thiomorpholin-4-yl-nicotinamide as a light beige powder.

Workup

  1. custompartitioned between ethyl acetate and half-saturated aqueous sodium chloride solution
  2. customThe phases are then separated
  3. washthe organic phase washed with half-saturated aqueous sodium chloride
  4. extractionThe aqueous phases are then extracted with ethyl acetate
  5. customThe combined organic extracts are dried
  6. concentrationconcentrated in a rotary evaporator
  7. customto produce a yellow oil
  8. customto obtain a refluxing suspension, which
  9. temperaturecan be cooled to room temperature
  10. stirringfurther stirred at 0° C. for about one hour
  11. filtrationThe precipitate is filtered off
  12. washwashed with cold n-hexane:ethyl acetate 9:1
  13. customdried in a vacuum oven

Sources & evidence

ORD record
ord-c5bed0ed805a4cd9b3ea13a8b8bfbe70
Source dataset
uspto-grants-2007_01
Patent number
US07160881B2

Reaction notes

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