HCID 2990663, compound → HCID 57656059, compound

HRID 911295Notes

Reaction equation

HRID 911295 reaction equation
[C:1]([C:3]1[CH:17]=[CH:16][C:6]([C:7]([NH:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:8])=[C:5]([F:18])[CH:4]=1)#[N:2]>N.CO.[Ni]>[NH2:2][CH2:1][C:3]1[CH:17]=[CH:16][C:6]([C:7]([NH:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:8])=[C:5]([F:18])[CH:4]=1

Participants

5

Reactant 1

HCID 2990663HCID 2990663, compound

Product 1

HCID 57656059HCID 57656059, compoundYield 95.9%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

Dissolve 4-cyano-N-cyclohexyl-2-fluoro-benzamide (620 mg, 2.5 mmol) in 7N ammonia in methanol (150 mL) and hydrogenate at 500 psi pressure in the presence of Raney® nickel (500 mg) for 16 h at 60° C. Filter the mixture and concentrate in vacuo. Purify by SCX chromatography to give the title compound as a white solid (600 mg, 94%). MS (ES−) m/z: 251 (M−H)−.

Workup

  1. filtrationFilter the mixture
  2. concentrationconcentrate in vacuo
  3. customPurify by SCX chromatography

Sources & evidence

ORD record
ord-193d531559534bb3914a425089fe9e72
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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