Sodium Hydroxide → HCID 56600792, compound

HRID 1187713Notes

Reaction equation

HRID 1187713 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([N:17]3[CH2:22][CH2:21][CH:20]([C:23]([O:25]CC)=[O:24])[CH2:19][CH2:18]3)[CH:14]=[C:13]([NH:28][C:29]3[CH:34]=[N:33][CH:32]=[CH:31][N:30]=3)[N:12]=2)[CH3:9])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([N:17]3[CH2:22][CH2:21][CH:20]([C:23]([OH:25])=[O:24])[CH2:19][CH2:18]3)[CH:14]=[C:13]([NH:28][C:29]3[CH:34]=[N:33][CH:32]=[CH:31][N:30]=3)[N:12]=2)[CH3:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 56600590HCID 56600590, compound

Product 1

HCID 56600792HCID 56600792, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

128 mg of ethyl (S)-1-{2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)pyrimidin-4-yl}piperidine-4-carboxylate (Example 83) was dissolved in 3 ml of ethanol, 0.28 ml of 12% sodium hydroxide aqueous solution was added thereto, and the mixture was stirred at room temperature for 6 hours. Ethanol was distilled off and then the obtained residue was diluted with water and the aqueous layer was washed with diethyl ether. The aqueous layer was neutralized with a 10% hydrochloric acid to pH 7 and subjected to extraction with ethyl acetate, and the organic layer was washed with brine, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was washed with diethyl ether, and filtered and dried under reduced pressure to obtain 58 mg of the objective compound as white powder.

Workup

  1. distillationEthanol was distilled off
  2. additionthe obtained residue was diluted with water
  3. washthe aqueous layer was washed with diethyl ether
  4. extractionsubjected to extraction with ethyl acetate
  5. washthe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. washthe obtained residue was washed with diethyl ether
  9. filtrationfiltered
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-f4750dcdff594a919e6d589bb78b523e
Source dataset
uspto-grants-2014_03
Patent number
US08673891B2

Reaction notes

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