Methane → tert-butyl 2-[2-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate

HRID 431598

반응식

HRID 431598 반응식
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:9][CH:8]=[CH:7][CH:6]=2.C(O[C:29](OCC)(OCC)[CH2:30][CH2:31][CH2:32][CH3:33])C.Cl.[NH+]1C=CC=CC=1.C>C1(C)C=CC=CC=1.CO>[CH2:30]([C:29]1[N:12]([CH2:13][CH2:14][O:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH2:31][CH2:32][CH3:33]

참가 물질

7

반응물 4

HCID 297MethaneHCID 701951,1,1-TriethoxypentaneHCID 12106200Tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy)ethylcarbamateHCID 21584435Pyridinium hydrochloride

생성물 1

HCID 21898025tert-butyl 2-[2-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate수율 99.9%

시약·촉매·용매 2

HCID 887Methanol용매HCID 1140Toluene용매

실험 절차

A solution of tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy}ethylcarbamate (3.46 g, 10.0 mmol) in 50 mL of toluene was treated with triethylorthovalerate (2.5 mL, 14.5 mmol) and the reaction mixture was heated to reflux. A 25 mg portion of pyridinium hydrochloride was then added and refluxing was continued for 4 h. The reaction was then concentrated to dryness under reduced pressure. The residue was dissolved in 50 mL of CH2Cl2 and washed with saturated NaHCO3, H2O and brine. The organic portion was dried over Na2SO4 and concetrated to give a green oil. The green oil was dissolved in 50 mL of hot MeOH and treated with activated charcoal. The hot solution was filtered and concentrated to give 4.12 g of tert-butyl 2-[2-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate as a yellow oil.

후처리

  1. temperaturethe reaction mixture was heated to reflux
  2. temperaturerefluxing
  3. concentrationThe reaction was then concentrated to dryness under reduced pressure
  4. dissolutionThe residue was dissolved in 50 mL of CH2Cl2
  5. washwashed with saturated NaHCO3, H2O and brine
  6. dry with materialThe organic portion was dried over Na2SO4
  7. customto give a green oil
  8. filtrationThe hot solution was filtered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d3feb39a66a149dda0c1419aa77a859d
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660747B2

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