1,1,1-Trimethoxybutane → 1-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

HRID 9447

반응식

HRID 9447 반응식
[C:1](OC)(OC)(OC)[CH2:2][CH2:3][CH3:4].Cl.N1C=CC=CC=1.[NH2:18][C:19]1[CH:20]=[N:21][C:22]2[C:27]([C:28]=1[NH:29][CH2:30][C:31]([CH3:34])([OH:33])[CH3:32])=[CH:26][CH:25]=[C:24]([Br:35])[CH:23]=2>C1(C)C=CC=CC=1>[Br:35][C:24]1[CH:25]=[CH:26][C:27]2[C:28]3[N:29]([CH2:30][C:31]([CH3:34])([OH:33])[CH3:32])[C:1]([CH2:2][CH2:3][CH3:4])=[N:18][C:19]=3[CH:20]=[N:21][C:22]=2[CH:23]=1

참가 물질

5

반응물 3

HCID 1235121,1,1-TrimethoxybutaneHCID 10176127Pyridinium chlorideHCID 219844571-(3-Amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol

생성물 1

HCID 219841831-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol수율 76.7%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Trimethyl orthobutyrate (11.61 mL, 72.6 mmol) and catalytic pyridine hydrochloride were added to a solution of 1-(3-amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol (22.51 g, 72.6 mmol) in anhydrous toluene (120 mL), and the reaction was heated at reflux for two hours. The solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was removed under reduced pressure until a precipitate began to form. Hexanes were added, and the precipitate was isolated by filtration to provide 20.17 g of 1-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol.

후처리

  1. temperaturethe reaction was heated
  2. temperatureat reflux for two hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washwashed with water
  6. customThe dichloromethane was removed under reduced pressure until a precipitate
  7. customto form
  8. customthe precipitate was isolated by filtration

출처 및 근거

ORD 기록
ord-dd064fe13c304d048f8985c83af1053f
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091214B2

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