Potassium Carbonate → 2-(methoxymethyl)-1-propyl-8-[3-(4-pyridin-2-ylpiperazin-1-yl)propoxy]-1H-imidazo[4,5-c]quinolin-4-amine

HRID 540962ノート

反応式

HRID 540962 の反応式
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[N:12]=[C:11]([NH2:16])[C:10]3[N:17]=[C:18]([CH2:23][O:24][CH3:25])[N:19]([CH2:20][CH2:21][CH3:22])[C:9]=3[C:8]=2[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1>CN(C=O)C>[CH3:25][O:24][CH2:23][C:18]1[N:19]([CH2:20][CH2:21][CH3:22])[C:9]2[C:8]3[CH:7]=[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:41]4[CH2:42][CH2:43][N:38]([C:33]5[CH:34]=[CH:35][CH:36]=[CH:37][N:32]=5)[CH2:39][CH2:40]4)[CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([NH2:16])[C:10]=2[N:17]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 944591-(2-Pyridyl)piperazineHCID 689690038-(3-chloropropoxy)-2-methoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine

生成物 1

HCID 588337172-(methoxymethyl)-1-propyl-8-[3-(4-pyridin-2-ylpiperazin-1-yl)propoxy]-1H-imidazo[4,5-c]quinolin-4-amine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A mixture of 8-(3-chloropropoxy)-2-(methoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine (0.20 g, 0.55 mmol, 1 equivalent), potassium carbonate (4 equivalents), and 1-(2-pyridyl)piperazine (1.1 equivalents) in DMF (5 mL) was heated at 70° C. overnight. The reaction mixture was allowed to cool to room temperature and was poured onto ice (50 g). After the mixture was stirred for 3 hours, a brown solid was isolated by filtration. The crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-30% CMA in chloroform), followed by recrystallization from acetonitrile to afford 0.065 g of 2-(methoxymethyl)-1-propyl-8-[3-(4-pyridin-2-ylpiperazin-1-yl)propoxy]-1H-imidazo[4,5-c]quinolin-4-amine as off white crystals, mp 196-197° C.

後処理

  1. temperatureto cool to room temperature
  2. additionwas poured onto ice (50 g)
  3. customa brown solid was isolated by filtration
  4. customThe crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-30% CMA in chloroform)
  5. customfollowed by recrystallization from acetonitrile

出典と根拠

ORDレコード
ord-374e540cf8f94cf49f12b1e9bd555a98
出典データセット
uspto-grants-2014_10
特許番号
US08871782B2

反応ノート

読み込み中…