Trimethyl orthovalerate → 2-butyl-1-(3-methylsulfanylpropyl)-7-phenyl-1H-imidazo[4,5-c]quinoline

HRID 9365

반응식

HRID 9365 반응식
[CH3:1][S:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[N:10]=[CH:9][C:8]=1[NH2:23].[C:24](OC)(OC)(OC)[CH2:25][CH2:26][CH2:27][CH3:28].Cl.N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:25]([C:24]1[N:6]([CH2:5][CH2:4][CH2:3][S:2][CH3:1])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:23]=1)[CH2:26][CH2:27][CH3:28]

참가 물질

5

반응물 3

HCID 83755Trimethyl orthovalerateHCID 10176127Pyridinium chlorideHCID 86593757N4-(3-methylsulfanylpropyl)-7-phenylquinoline-3,4-diamine

생성물 1

HCID 219844302-butyl-1-(3-methylsulfanylpropyl)-7-phenyl-1H-imidazo[4,5-c]quinoline수율 90.7%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

N4-(3-Methylsulfanylpropyl)-7-phenylquinoline-3,4-diamine (2.75 g, 8.49 mmol), trimethyl orthovalerate (1.7 g, 10 mmol), and pyridine hydrochloride (0.3 g) were dissolved in toluene (28 mL) and heated to reflux for 1.5 h, collecting the volatiles in a Dean—Stark trap. Upon cooling to room temperature, the solvent was removed under vacuum. The resulting solid was slurried in hexanes (100 mL) for 1 h and then collected by filtration to afford 3.0 g of 2-butyl-1-(3-methylsulfanylpropyl)-7-phenyl-1H-imidazo[4,5-c]quinoline.

후처리

  1. temperatureheated
  2. temperatureto reflux for 1.5 h
  3. customcollecting the volatiles in a Dean—Stark trap
  4. customthe solvent was removed under vacuum
  5. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-db8fbeb70dec4320954face4762c20da
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091214B2

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