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

HRID 81907Notes

Reaction equation

HRID 81907 reaction equation
Cl.[Br:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:20][CH2:21][C:22]([OH:25])([CH3:24])[CH3:23])=[C:8]([NH:13][C:14](=O)[CH2:15][CH2:16][O:17][CH3:18])[CH:9]=[N:10]2)=[N:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].O.C>C(Cl)(Cl)Cl.CO.C(O)C>[Br:2][C:3]1[CH:4]=[N:5][C:6]2[C:7]3[N:20]([CH2:21][C:22]([CH3:24])([OH:25])[CH3:23])[C:14]([CH2:15][CH2:16][O:17][CH3:18])=[N:13][C:8]=3[CH:9]=[N:10][C:11]=2[CH:12]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 962WaterHCID 11430Potassium CarbonateHCID 67052276N-{7-bromo-4-[(2-hydroxy-2-methylpropyl)amino][1,5]naphthyridin-3-yl}-3-methoxypropionamide hydrochloride

Product 1

HCID 670525301-[7-bromo-2-(2-methoxyethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-olYield 73.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21584188Chloroform methanolSolvent

Procedure

A mixture of N-{7-bromo-4-[(2-hydroxy-2-methylpropyl)amino][1,5]naphthyridin-3-yl}-3-methoxypropionamide hydrochloride (60.00 g, 138 mmol), potassium carbonate (60 g), water (300 mL), and ethanol (900 mL) was heated at reflux for 16 hours and then concentrated under reduced pressure. The precipitated solid was isolated by filtration, washed sequentially with water and methanol, and dried to provide a brown solid. This material was dissolved in a 3/1 mixture of chloroform/methanol and decolorized with activated charcoal to provide 38.5 g of 1-[7-bromo-2-(2-methoxyethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol as a white solid, mp 125° C. Anal. calcd for C16H19BrN4O2: % C, 50.67; % H, 5.05; % N, 14.77. Found: % C, 50.86; % H, 4.94; % N, 15.01.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe precipitated solid was isolated by filtration
  5. washwashed sequentially with water and methanol
  6. customdried
  7. customto provide a brown solid

Sources & evidence

ORD record
ord-3059ef6d2a02420f82af82b8f1ea029a
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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