HCID 68933218, compound → HCID 68992892, compound

HRID 81890Notes

Reaction equation

HRID 81890 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][C:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:18])[CH3:17])=[N:11][CH:10]=[CH:9][CH:8]=2)([O-])=O.[H][H]>C(#N)C.[Pt]>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][C:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:17])[CH3:18])=[N:11][CH:10]=[CH:9][CH:8]=2

Participants

5

Reactant 2

HCID 68933218HCID 68933218, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68992892HCID 68992892, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 23939PlatinumSolvent

Procedure

A Parr vessel was charged with a solution of tert-butyl N-{2-[(3-nitro[1,5]naphthyridin-4-yl)amino]-1,1-dimethylethyl}carbamate (12.62 g, 34.9 mmol) in acetonitrile (100 mL) and 5% Pt/C (2.00 g). The vessel was placed under hydrogen pressure (50 psi, 3.4×105 Pa) until hydrogen uptake ceased. The reaction mixture was filtered through a layer of CELITE filter aid and the filter cake was rinsed with acetonitrile. The filtrate was concentrated under reduced pressure to provide 11.07 g of tert-butyl N-{2-[(3-amino[1,5]naphthyridin-4-yl)amino]-1,1-dimethylethyl]carbamate as a bright yellow foam.

Workup

  1. filtrationThe reaction mixture was filtered through a layer of CELITE
  2. filtrationfilter aid
  3. washthe filter cake was rinsed with acetonitrile
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-658ef3cdb3f144b4867930bfb0e57b9d
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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