Ammonia → HCID 70570674, compound

HRID 2403585Notes

Reaction equation

HRID 2403585 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([CH3:28])[C:17](=[O:27])[CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:10]=2)=[CH:5][CH:4]=1)#[N:2].N>CO.[Ni]>[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([CH3:28])[C:17](=[O:27])[CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:25])[CH3:23])[CH:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 70570449HCID 70570449, compound

Product 1

HCID 70570674HCID 70570674, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl (2-{[(4′-cyanobiphenyl-3-yl)methyl](methyl)amino}-2-oxoethyl)carbamate (1.3 g) was dissolved in MeOH (20 ml), and a 28% aqueous ammonia solution (2 ml) was added thereto. Then, Raney nickel (205 mg) was added thereto under an argon atmosphere, followed by stirring at room temperature overnight under a hydrogen atmosphere at 1 atm. The reaction mixture was filtered and washed with water, and then the filtrate was extracted with CHCl3. The organic layer was concentrated under reduced pressure, and then the obtained residue was purified by silica gel column chromatography (0 to 10% MeOH/CHCl3) to obtain tert-butyl {2-[{[4′-(aminomethyl)biphenyl-3-yl]methyl}(methyl)amino]-2-oxoethyl}carbamate (900 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with water
  3. extractionthe filtrate was extracted with CHCl3
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (0 to 10% MeOH/CHCl3)

Sources & evidence

ORD record
ord-1e7ea9ab0c36427c9d84ff6f577facf1
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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