Ammonia → 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine
Reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([CH3:28])[N:14]([CH2:15][C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)[CH:17]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:29]>CO>[F:27][C:24]1[CH:25]=[CH:26][C:21]([C:18]2[CH:17]=[C:16]([CH2:15][N:14]3[C:10]4[C:9]5[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=5[N:3]=[C:2]([NH2:29])[C:11]=4[N:12]=[C:13]3[CH3:28])[O:20][N:19]=2)=[CH:22][CH:23]=1Participants
Procedure
4-Chloro-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-2-methyl-1H-imidazo[4,5-c]quinoline (2.307 g, 5.873 mmol) was treated according to the method described in Part B of Example 27 using 60 mL of 7 N ammonia in methanol. Following the purification steps, the solid product was stirred for 16 hours in 25% potassium hydroxide in ethanol, isolated by filtration, washed with water and isopropyl alcohol, and dried. The resulting white solid was stirred for one hour with 6 N hydrogen chloride in ethanol, and the mixture was then adjusted to pH 14 with the addition of 6 N potassium hydroxide. The solid was isolated by filtration, washed with water and diethyl ether, and dried under high vacuum at 100° C. for 18 hours to provide 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine as a white powder, mp 294.0-296.0° C.
Workup
- customthe purification steps
- customisolated by filtration
- washwashed with water and isopropyl alcohol
- customdried
- stirringThe resulting white solid was stirred for one hour with 6 N hydrogen chloride in ethanol
- additionthe mixture was then adjusted to pH 14 with the addition of 6 N potassium hydroxide
- customThe solid was isolated by filtration
- washwashed with water and diethyl ether
- customdried under high vacuum at 100° C. for 18 hours
Sources & evidence
- ORD record
- ord-6e4ffb8191ab449c9b7444e76b34e591
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07915281B2
Reaction notes
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