HCID 22172707, compound → Tert-butyl 4-[(3-amino[1,5]naphthyridin-4-yl)amino]butylcarbamate

HRID 497759Notes

Reaction equation

HRID 497759 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[N:11][CH:10]=[CH:9][CH:8]=2)([O-])=O.[H][H]>[Pt].C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[N:11][CH:10]=[CH:9][CH:8]=2

Participants

5

Reactant 2

HCID 22172707HCID 22172707, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22172729Tert-butyl 4-[(3-amino[1,5]naphthyridin-4-yl)amino]butylcarbamate

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1,1-Dimethylethyl N-{4-[(3-nitro[1,5]naphthyridin-4-yl)amino]butyl}carbamate (42.7 g, 0.12 mole), platinum on carbon (2 g) and ethyl acetate (500 mL) were combined and then hydrogenated on a Parr apparatus at 30 psi (2.1 Kg/cm2) hydrogen pressure for 1 hour. The catalyst was removed by filtration and rinsed with ethyl acetate. The filtrate was concentrated under vacuum to provide 1,1-dimethylethyl N-{4-[(3-amino[1,5]naphthyridin-4-yl)amino]butyl}carbamate as a bright yellow-orange solid.

Workup

  1. customThe catalyst was removed by filtration
  2. washrinsed with ethyl acetate
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-da826451ec904f90ae945bcd218601d9
Source dataset
uspto-grants-2005_09
Patent number
US06949646B2

Reaction notes

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