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

HRID 9350

반응식

HRID 9350 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 10176127Pyridinium chloride촉매HCID 1140Toluene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-162be3fc5e3f4ed98a5683cec7677ead
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091214B2

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