Acetate → HCID 22248353, compound

HRID 890119Notes

Reaction equation

HRID 890119 reaction equation
C([O-])(=O)C.C([O:9][C:10]1[C:11]([CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([CH:23]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[F:33])[C:24]#[N:25])[CH2:19][CH2:18]2)=[N:12][CH:13]=[CH:14][N:15]=1)(C)(C)C.[OH-].[Na+]>C(OCC)(=O)C>[F:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH2:26][CH:23]([CH:20]1[CH2:19][CH2:18][N:17]([CH2:16][C:11]2[C:10](=[O:9])[NH:15][CH:14]=[CH:13][N:12]=2)[CH2:22][CH2:21]1)[C:24]#[N:25]

Participants

5

Reactant 3

HCID 175AcetateHCID 14798Sodium HydroxideHCID 22248171HCID 22248171, compound

Product 1

HCID 22248353HCID 22248353, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

After adding 3 ml of 4N hydrogen chloride/ethyl is acetate to 188 mg of 2-[1-(3-tert-butoxy-2-pyrazinylmethyl)piperidin-4-yl]-3-(2-fluorophenyl)propionitrile while cooling on ice, the mixture was stirred 1 hour. A 2N sodium hydroxide solution was added to the reaction solution for neutralization, and extraction was performed with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. Diethyl ether was added to the residue and the mixture was filtered to obtain the title compound (129 mg, 80% yield).

Workup

  1. additionAfter adding 3 ml of 4N hydrogen chloride/ethyl
  2. temperaturewhile cooling on ice
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionDiethyl ether was added to the residue
  7. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-e7c1274cbbf54b7c95cb97be4d9a8fe3
Source dataset
uspto-grants-2006_02
Patent number
US06995144B2

Reaction notes

Loading…