Ethanol → 7-Bromo-2-ethoxymethyl-1-(isopropoxypropyl)-1H-imidazo[4,5-c]quinoline

HRID 909337

반응식

HRID 909337 반응식
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:13][CH2:14][CH2:15][CH2:16][O:17][CH:18]([CH3:20])[CH3:19])=[C:7]([NH2:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH2:21]([O:23][CH2:24][C:25](Cl)=O)[CH3:22].C(O)C>C(#N)C.C(N(CC)CC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:13]([CH2:14][CH2:15][CH2:16][O:17][CH:18]([CH3:20])[CH3:19])[C:22]([CH2:21][O:23][CH2:24][CH3:25])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1

참가 물질

6

반응물 3

HCID 702EthanolHCID 84189Ethoxyacetyl chlorideHCID 690787337-bromo-N4-(3-isopropoxypropyl)quinoline-3,4-diamine

생성물 1

HCID 673819647-Bromo-2-ethoxymethyl-1-(isopropoxypropyl)-1H-imidazo[4,5-c]quinoline수율 67.1%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8471Triethylamine용매2회

실험 절차

7-Bromo-N4-(3-isopropoxypropyl)quinoline-3,4-diamine (45 g) was dissolved in acetonitrile (1.3 L) and triethylamine (19.4 mL). Ethoxyacetyl chloride (18.0 g) was added dropwise to the solution and the reaction was stirred for 16 hours. The solvent was removed under reduced pressure to afford a tan solid. The solid was added to a solution of ethanol (1 L) and triethylamine (77.5 mL) and heated at reflux for 4 hours. The solvent was removed under reduced pressure. Water was added to the solid residue and the crude product was recovered by filtration. Recrystallization from acetonitrile yielded 36.25 g of 7-bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinoline as a tan crystalline solid.

후처리

  1. customThe solvent was removed under reduced pressure
  2. customto afford a tan solid
  3. temperatureheated
  4. temperatureat reflux for 4 hours
  5. customThe solvent was removed under reduced pressure
  6. additionWater was added to the solid residue
  7. filtrationthe crude product was recovered by filtration
  8. customRecrystallization from acetonitrile

출처 및 근거

ORD 기록
ord-134fed903e6046ffa77168d789ca7fdf
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017779B2

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