Process for preparing 2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-C][1,5]naphthyridin-4-amine
A kind of methylpropyl, imidazo technology, applied in the direction of organic chemistry etc.
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Examples
Embodiment 1
[0096] Example 1 prepares N 4 -(2-Methylpropyl)-3-nitro[1,5]naphthyridin-4-amine
[0097] Part A
[0098] A suspension of 3-nitro[1,5]naphthyridine-4-ol (12.00 kg, 67.78 mol) in DMF (49 L) was stirred at a temperature of 20°C to 24°C for 30 minutes under a nitrogen atmosphere. Phosphorus oxychloride (10.6 kg, 69.1 mol) was added slowly over 53 minutes while maintaining the temperature at 20.6°C to 25.6°C. Additional DMF (5 L) was used to rinse the addition vessel and added to the reaction. The reaction was stirred at a temperature of 20°C to 24°C for 19 hours and 17 minutes, then added rapidly over four minutes to purified water (275 L) which had been cooled to 8.4°C. During the addition, the temperature of the mixture did not exceed 18°C. Additional water (80 L) was used to rinse the initial container and was added quickly to the resulting mixture, which temperature during the addition ranged from 16.6°C to 17.2°C. The mixture resulting from the addition was stirred for ...
Embodiment 2
[0101] Embodiment 2 prepares N 4 -(2-Methylpropyl)-3-nitro[1,5]naphthyridin-4-amine
[0102] Part A
[0103]A suspension of 3-nitro[1,5]naphthyridin-4-ol (1.00 kg, 5.23 mol) in DMF (4.5 L) was cooled in an ice bath under a nitrogen atmosphere. Phosphorus oxychloride (882.5 g, 5.75 mol) was added slowly over one hour while maintaining the temperature between 16°C and 20°C. After the addition was complete, the reaction was stirred at a temperature of 20°C to 24°C for three hours, then rapidly added to two portions of demineralized water (12.5 L each) at a temperature of 20°C to 24°C. During this addition, the temperature of the mixture was brought to 29.5°C to 30.5°C. The resulting mixture was cooled to a temperature of about 10°C over 60 minutes. The solids formed in the individual mixtures were isolated by filtration and each solid was washed with demineralized water (2 x 2 L and 1 x 1 L) until the pH of the filtrate was equal to that of demineralized water. The brown sol...
Embodiment 3
[0106] Example 3 Preparation of 2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridine-5-oxide
[0107] Part A
[0108] Supply N to the hydrogenation vessel 4 -(2-Methylpropyl)-3-nitro[1,5]naphthyridin-4-amine (7.50 kg, 30.5 mol) and toluene (125.0 kg). A suspension of 3% platinum on carbon (0.44 kg, about 33 wt% (w / w) in water) in isopropanol (7.0 kg) was added to the vessel followed by rinsing with toluene (10.0 kg). Then the reaction mixture was heated under hydrogen pressure (2.4×10 5 Pa, 2.4 bar) for six hours while stirring and maintaining a temperature of 22°C. The reaction mixture was then filtered and the filter cake was washed with toluene (30.0 kg). Reduced pressure at about 50°C (1×10 4 pa, 0.1 bar) to concentrate the filtrate to provide N 4 -(2-methylpropyl)[1,5]naphthyridine-3,4-diamine in toluene (75 L, about 10 mL / g) solution.
[0109] Part B
[0110] The solution from Part A (75 L) was heated to 50 °C and p-toluenesulfonic acid monohydrate (0....
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