HCID 57656058, compound → HCID 57655921, compound

HRID 911627Notes

Reaction equation

HRID 911627 reaction equation
[C:1]([C:3]1[CH:17]=[CH:16][C:6]([C:7]([NH:9][C@H:10]([CH3:15])[C:11]([F:14])([F:13])[F:12])=[O:8])=[C:5]([F:18])[CH:4]=1)#[N:2]>C(O)C.O.C(O)(=O)C.[Pd]>[NH2:2][CH2:1][C:3]1[CH:17]=[CH:16][C:6]([C:7]([NH:9][C@H:10]([CH3:15])[C:11]([F:12])([F:13])[F:14])=[O:8])=[C:5]([F:18])[CH:4]=1

Participants

6

Reactant 1

HCID 57656058HCID 57656058, compound

Product 1

HCID 57655921HCID 57655921, compoundYield 94%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Combine a solution of (R)-4-cyano-2-fluoro-N-(2,2,2-trifluoro-1-methyl-ethyl)-benzamide (0.904 g, 3.475 mmol) in absolute ethanol (26 mL), water (9.7 mL) and glacial acetic acid (1.2 mL) with 10% Pd/C (Degussa type E101, 0.27 g, 0.13 mmol) under nitrogen. Purge the mixture with nitrogen and then with hydrogen. Stir the slurry at room temperature under hydrogen at 55 psi for 30 min. Purge the reaction mixture with nitrogen and then filter the slurry over Celite®. Wash the filter cake with ethanol (100 mL) and THF (100 mL). Concentrate the filtrate and purify by SCX chromatography eluting with dichloromethane/methanol (1:1) to remove impurities and then with dichloromethane/2M ammonia in methanol (1:1) to elute product. Concentrate to afford the title compound as a colorless oil (0.86 g, 94%).

Workup

  1. customPurge the mixture with nitrogen
  2. customPurge the reaction mixture with nitrogen
  3. filtrationfilter the slurry over Celite®
  4. washWash the filter cake with ethanol (100 mL) and THF (100 mL)
  5. concentrationConcentrate the filtrate
  6. custompurify by SCX chromatography
  7. washeluting with dichloromethane/methanol (1:1)
  8. customto remove impurities
  9. washwith dichloromethane/2M ammonia in methanol (1:1) to elute product
  10. concentrationConcentrate

Sources & evidence

ORD record
ord-79d940d4b4ed408194b09cddc34dc8e9
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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