Ammonia → 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine

HRID 606109Notes

Reaction equation

Cl[C:2]1[C:11]2[N:12]=[C:13]([CH2:28][CH2:29][CH3:30])[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.[NH3:31]>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]([NH2:31])[C:11]=4[N:12]=[C:13]3[CH2:28][CH2:29][CH3:30])[O:20][N:19]=2)=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-chloro-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-2-propyl-1H-imidazo[4,5-c]quinoline (0.806 g, 1.92 mmol) and 7 N ammonia in methanol (40 mL) was sealed in a pressure vessel and heated at 150° C. for 18 hours and allowed to cool to room temperature. The volatiles were removed under reduced pressure, and the resulting solid was stirred with 0.5 N sodium hydroxide in methanol. The solid was isolated by filtration, washed with diethyl ether, purified by column chromatography on silica gel (eluting with 5% to 10% CMA in chloroform), triturated with diethyl ether, isolated by filtration, and dried to provide 0.123 g of 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine as a white powder, mp 226.0-227.0° C.

Workup

customwas sealed in a pressure vessel
temperatureto cool to room temperature
customThe volatiles were removed under reduced pressure
customThe solid was isolated by filtration
washwashed with diethyl ether
custompurified by column chromatography on silica gel (eluting with 5% to 10% CMA in chloroform)
customtriturated with diethyl ether
customisolated by filtration
customdried

Sources & evidence

ORD record: ord-9116ff7050eb41959106330d7b5e9dfb
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915281B2

Reaction notes

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