HCID 58081198, compound → N-[5-(aminomethyl)-4,6-dimethyl(2-pyridyl)] (tert-butoxy)carboxamide

HRID 928404Notes

Reaction equation

HRID 928404 reaction equation
[C:1]([C:3]1[C:4]([CH3:18])=[CH:5][C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[N:7][C:8]=1[CH3:9])#[N:2]>CO.N.[Ni]>[NH2:2][CH2:1][C:3]1[C:4]([CH3:18])=[CH:5][C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[N:7][C:8]=1[CH3:9]

Participants

4

Reactant 1

HCID 58081198HCID 58081198, compound

Product 1

HCID 22475372N-[5-(aminomethyl)-4,6-dimethyl(2-pyridyl)] (tert-butoxy)carboxamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

tert-butyl 5-cyano-4,6-dimethylpyridin-2-ylcarbamate (8 g) was hydrogenated by means of raney-nickel (18.9 g) in MeOH/NH3 aq. 10% (100 ml). The reaction mixture was filtered through hyflo, washed with MeOH and evaporated under reduced pressure. The crude was solved in EA (100 ml) and heptane 80 (ml) was added. The solution was partly evaporated to a volume of approx. 80 ml. The precipitated solid was filtrated to afford the title compound. HPLC/MS (Method F): RtF=0.82 min, [M+H]+=252.3.

Workup

  1. filtrationThe reaction mixture was filtered through hyflo
  2. washwashed with MeOH
  3. customevaporated under reduced pressure
  4. additionheptane 80 (ml) was added
  5. customThe solution was partly evaporated to a volume of approx. 80 ml
  6. filtrationThe precipitated solid was filtrated

Sources & evidence

ORD record
ord-9a90fea16a9a426da05be65389ac435b
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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