Trimethyl orthovalerate → 7-bromo-2-butyl-1-isobutyl-1H-imidazo[4,5-c]quinoline

HRID 9350

反応式

HRID 9350 の反応式
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[C:7]([NH2:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[C:18](OC)(OC)(OC)[CH2:19][CH2:20][CH2:21][CH3:22]>Cl.N1C=CC=CC=1.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:18]([CH2:19][CH2:20][CH2:21][CH3:22])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1

参加物

5

反応物 2

HCID 83755Trimethyl orthovalerateHCID 688181597-bromo-N4-isobutylquinoline-3,4-diamine

生成物 1

HCID 219843597-bromo-2-butyl-1-isobutyl-1H-imidazo[4,5-c]quinoline収率 43.9%

試薬・触媒・溶媒 2

HCID 10176127Pyridinium chloride触媒HCID 1140Toluene溶媒

実験手順

7-Bromo-N4-isobutylquinoline-3,4-diamine (39.4 g of crude material), trimethyl orthovalerate (32 g, 0.20 mol), and pyridine hydrochloride (0.31 g, 2.7 mmol) were combined with anhydrous toluene (500 mL) and heated to reflux for 30 min. The reaction was cooled to room temperature, concentrated, and the residue was purified by chromatography on silica gel (75% ethyl acetate in hexane to 100% ethyl acetate gradient) to afford 21.2 g of 7-bromo-2-butyl-1-isobutyl-1H-imidazo[4,5-c]quinoline as a yellow solid.

後処理

  1. temperatureheated
  2. temperatureto reflux for 30 min
  3. concentrationconcentrated
  4. customthe residue was purified by chromatography on silica gel (75% ethyl acetate in hexane to 100% ethyl acetate gradient)

出典と根拠

ORDレコード
ord-162be3fc5e3f4ed98a5683cec7677ead
出典データセット
uspto-grants-2006_08
特許番号
US07091214B2

関連ノート

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