N-(2-fluoro-2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine → HCID 86626701, compound

HRID 81933Notes

Reaction equation

HRID 81933 reaction equation
[F:1][C:2]([CH3:19])([CH3:18])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[N:8]=[CH:7][C:6]=1[N+:15]([O-])=O>C(#N)C.[Pt]>[F:1][C:2]([CH3:19])([CH3:18])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[N:8]=[CH:7][C:6]=1[NH2:15]

Participants

4

Reactant 1

HCID 68934906N-(2-fluoro-2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine

Product 1

HCID 86626701HCID 86626701, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of N-(2-fluoro-2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine (2.64 g, 10.0 mmol) dissolved in 80 mL of acetonitrile was placed in a pressure bottle. Platinum on carbon (5%, 500 mg) was then added and the reaction mixture was shaken under H2 at 50 PSI (3.4×105 Pa). After 5 hours, the reaction mixture was filtered through a pad of CELITE filter agent. The pad was rinsed with acetonitrile and the combined filtrates were concentrated under reduced pressure to give 2.12 g of N4-(2-fluoro-2-methylpropyl)[1,5]naphthyridine-3,4-diamine as a brown foam.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washThe pad was rinsed with acetonitrile
  4. concentrationthe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-7ce1dd69866e436d89c4b909b0cce0cb
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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