1-[(7-Bromo-3-nitro[1,5]naphthyridin-4-yl)amino]-2-methylpropan-2-ol → 1-[(3-Amino-7-bromo[1,5]naphthyridin-4-yl)amino]-2-methylpropan-2-ol

HRID 598032Notes

Reaction equation

HRID 598032 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][CH2:16][C:17]([CH3:20])([OH:19])[CH3:18])=[C:7]([N+:12]([O-])=O)[CH:8]=[N:9]2)=[N:4][CH:3]=1>[Pt].C(#N)C.CO>[NH2:12][C:7]1[CH:8]=[N:9][C:10]2[C:5]([C:6]=1[NH:15][CH2:16][C:17]([CH3:18])([OH:19])[CH3:20])=[N:4][CH:3]=[C:2]([Br:1])[CH:11]=2

Participants

5

Reactant 1

HCID 670524611-[(7-Bromo-3-nitro[1,5]naphthyridin-4-yl)amino]-2-methylpropan-2-ol

Product 1

HCID 670523831-[(3-Amino-7-bromo[1,5]naphthyridin-4-yl)amino]-2-methylpropan-2-olYield 99.6%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A Parr vessel was charged with 5% platinum on carbon (5.8 g) and a suspension of 1-[(7-bromo-3-nitro[1,5]naphthyridin-4-yl)amino]-2-methylpropan-2-ol (58.00 g) in acetonitrile (800 mL) and methanol (400 mL). The vessel was placed under hydrogen pressure (30 psi, 2.1×105 Pa) for 8 hours. The reaction mixture was filtered through a layer of CELITE filter aid. The filtrate was concentrated under reduced pressure to provide 52.70 g of 1-[(3-amino-7-bromo[1,5]naphthyridin-4-yl)amino]-2-methylpropan-2-ol as a yellow solid.

Workup

  1. customfor 8 hours
  2. filtrationThe reaction mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5c140876f1694237abb22e2665c4e66b
Source dataset
uspto-grants-2011_03
Patent number
US07897609B2

Reaction notes

Loading…