Ammonia → 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinolin-4-amine

HRID 606105Notes

Reaction equation

HRID 606105 reaction equation
Cl[C:2]1[C:11]2[N:12]=[CH:13][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.[NH3:28]>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]([NH2:28])[C:11]=4[N:12]=[CH:13]3)[O:20][N:19]=2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 590266744-chloro-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinoline

Product 1

HCID 590267011-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-chloro-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinoline (0.2322 g, 0.6130 mmol) and 7 N ammonia in methanol (10 mL) was sealed in a pressure vessel and heated at 150° C. for 22 hours and allowed to cool to room temperature. The volatiles were removed under reduced pressure, and the resulting orange solid was triturated with diethyl ether. The solid was then purified by column chromatography on silica gel (7 g, eluting with 10% to 20% CMA in chloroform), triturated with diethyl ether, isolated by filtration, and dried. The solid was then boiled in methanol in the presence of a small amount of 0.5 N sodium hydroxide in methanol. The mixture was allowed to cool to room temperature, and the solid was isolated by filtration and dried to provide 0.0259 g of 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinolin-4-amine as a tan powder, mp 259.0-260.0° C.

Workup

  1. customwas sealed in a pressure vessel
  2. temperatureto cool to room temperature
  3. customThe volatiles were removed under reduced pressure
  4. customthe resulting orange solid was triturated with diethyl ether
  5. customThe solid was then purified by column chromatography on silica gel (7 g, eluting with 10% to 20% CMA in chloroform)
  6. customtriturated with diethyl ether
  7. customisolated by filtration
  8. customdried
  9. temperatureto cool to room temperature
  10. customthe solid was isolated by filtration
  11. customdried

Sources & evidence

ORD record
ord-39019b92f57c4cb2a3425e6d647b9291
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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