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

HRID 1818115

反応式

HRID 1818115 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c0cd15c2230a47309c6c01de86410bfe
出典データセット
uspto-grants-2009_10
特許番号
US07598382B2

関連ノート

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