1-[4-amino-7-bromo-2-(2-methoxyethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol → 1-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol hydrobromide

HRID 81908Notes

Reaction equation

HRID 81908 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][CH2:21][O:22][CH3:23])[N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:10]=2[C:9]2[N:8]=[CH:7][C:6]([Br:24])=[CH:5][C:4]=2[N:3]=1>C(#N)C.CO.C(Cl)(Cl)Cl.CO.[Pd]>[BrH:24].[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][CH2:21][O:22][CH3:23])[N:14]([CH2:15][C:16]([CH3:17])([OH:18])[CH3:19])[C:10]=2[C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

6

Reactant 1

HCID 589707001-[4-amino-7-bromo-2-(2-methoxyethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol

Product 1

HCID 689369541-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol hydrobromideYield 88.3%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 21584188Chloroform methanolSolvent

Procedure

A Parr vessel was charged with 10% Pd/C (0.6 g) and a suspension of 1-[4-amino-7-bromo-2-(2-methoxyethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol (4.0 g) in acetonitrile (150 mL) and methanol (50 mL). The vessel was placed under hydrogen pressure (50 psi, 3.4×105 Pa) for 3 hours. The reaction mixture was diluted with 1/1 chloroform/methanol (100 mL), filtered through a layer of CELITE filter aid, and concentrated under reduced pressure. The residue was triturated with acetonitrile to provide 3.55 g of 1-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol hydrobromide as a white powder, mp 234-235° C. Anal. calcd for C16H22BrN5O2: % C, 48.49; % H, 5.60; % N, 17.67. Found: % C, 48.64; % H, 5.69; % N, 17.62.

Workup

  1. customfor 3 hours
  2. filtrationfiltered through a layer of CELITE
  3. filtrationfilter aid
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was triturated with acetonitrile

Sources & evidence

ORD record
ord-cf6f6e90181249b7b6a2764315b9e1a2
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

Loading…