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

HRID 606109ノート

反応式

HRID 606109 の反応式
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

参加物

4

反応物 2

HCID 222AmmoniaHCID 866168924-chloro-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-2-propyl-1H-imidazo[4,5-c]quinoline

生成物 1

HCID 590266971-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-9116ff7050eb41959106330d7b5e9dfb
出典データセット
uspto-grants-2011_03
特許番号
US07915281B2

反応ノート

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