Ammonium formate → HCID 18536388, compound

HRID 412586Notes

Reaction equation

HRID 412586 reaction equation
C(OC([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][C:15]([O:21][CH2:22][CH2:23][C:24]3([C:36]#[N:37])[CH2:29][CH2:28][N:27]([C:30]4[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=4)[CH2:26][CH2:25]3)=[CH:16][CH:17]=2)[CH2:12]1)=O)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[C].[Pd]>[C:36]([C:24]1([CH2:23][CH2:22][O:21][C:15]2[CH:14]=[C:13]3[C:18]([CH2:19][CH2:20][NH:11][CH2:12]3)=[CH:17][CH:16]=2)[CH2:25][CH2:26][N:27]([C:30]2[CH:31]=[CH:32][N:33]=[CH:34][CH:35]=2)[CH2:28][CH2:29]1)#[N:37]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 60064146HCID 60064146, compound

Product 1

HCID 18536388HCID 18536388, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 7-[2-[4-cyano-1-(pyridin-4-yl)piperidin-4-yl]ethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid benzyl ester (585 mg) in ethanol (5 ml) were added 7.5% palladium carbon (220 mg) and ammonium formate (220 mg), and the mixture was stirred under reflux for 3 hours. After completion of the reaction, the reaction mixture was filtrated and the solvent was evaporated. To the obtained residue was added aqueous sodium hydrogencarbonate and the mixture was extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was dried under reduced pressure to give the title compound (385 mg).

Workup

  1. temperatureunder reflux for 3 hours
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtrated
  4. customthe solvent was evaporated
  5. additionTo the obtained residue was added aqueous sodium hydrogencarbonate
  6. extractionthe mixture was extracted with chloroform
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated
  10. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-4a74fe16a0484c7db1fd66c66849ac24
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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