HCID 15463557, compound → HCID 15463561, compound

HRID 1005457Notes

Reaction equation

HRID 1005457 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[NH:13][C:12](=[O:14])[C:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[H][H]>[Ni].CO>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([C:9]2[NH:13][C:12](=[O:14])[C:11]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 15463557HCID 15463557, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15463561HCID 15463561, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a glass bomb was added 100 mg (0.296 mmol) of the compound of Example 2, the 3-cyanophenyl derivative, and 10 mg of freshly washed Raney nickel in 6 mL of a 5:1 MeOH:NH4OH(conc.) solution. The reaction vessel was charged with 50 psi hydrogen and shaken overnight. Upon completion the reaction was filtered through Celite and the solvent was evaporated in vacuo. Chromatography of the crude solid (Silica gel/Hexanes:Acetone 2:1) produced 65 mg (64%) of the desired amine as an off-white solid. LRMS m/z (ESI) 342.3 (M+H).

Workup

  1. filtrationUpon completion the reaction was filtered through Celite
  2. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-2373b9c05c6b4d84bbf600e3890d1e9c
Source dataset
uspto-grants-2000_04
Patent number
US06054590

Reaction notes

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