Phenyl isocyanate → N-{8-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]octyl}-N'-phenylurea

HRID 2182298ノート

反応式

HRID 2182298 の反応式
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:22]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[C:14]([NH2:23])[C:13]=2[N:12]=[C:11]1[CH2:24][CH2:25][O:26][CH3:27].[C:28]1([N:34]=[C:35]=[O:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl>[NH2:23][C:14]1[C:13]2[N:12]=[C:11]([CH2:24][CH2:25][O:26][CH3:27])[N:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:35]([NH:34][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:36])[C:22]=2[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=1

参加物

4

反応物 2

HCID 7672Phenyl isocyanateHCID 223444471-(8-Aminooctyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine

生成物 1

HCID 11755253N-{8-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]octyl}-N'-phenylurea

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Under a nitrogen atmosphere a mixture of 1-(8-aminooctyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine (1.5 g, 4.06 mmol) and dichloromethane (50 mL) was cooled to 0° C. Phenyl isocyanate was added dropwise. The reaction mixture was allowed to slowly warm to ambient temperature overnight. The reaction mixture was concentrated under reduced pressure. The crude product was purified by column chromatography (110 g silica gel eluting with 9:1 dichloromethane:methanol). The resulting orange solid was triturated with hexanes, isolated by filtration and then dried. This material was recrystallized from propyl acetate with a small amount of methanol, isolated by filtration, washed with hexanes, and then dried in a vacuum oven at 60° C. for 2 days to provide 0.6 g of N-{8-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]octyl}-N′-phenylurea as an off white powder, m.p. 136-142° C. Analysis: Calculated for C28H36N6O2: % C, 68.83; % H, 7.43; % N, 17.20. Found: % C, 68.27; % H, 7.44; % N, 16.85.

後処理

  1. temperatureto slowly warm to ambient temperature overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe crude product was purified by column chromatography (110 g silica gel eluting with 9:1 dichloromethane:methanol)
  4. customThe resulting orange solid was triturated with hexanes
  5. customisolated by filtration
  6. customdried
  7. customThis material was recrystallized from propyl acetate with a small amount of methanol
  8. customisolated by filtration
  9. washwashed with hexanes
  10. customdried in a vacuum oven at 60° C. for 2 days

出典と根拠

ORDレコード
ord-947f4f1216e2448bb3385793ee2d1bd3
出典データセット
uspto-grants-2005_05
特許番号
US06897221B2

反応ノート

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