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

HRID 2203639노트

반응식

HRID 2203639 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e9ffa30c71a2424e8f5805c8accc7ec0
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365567B2

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