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

HRID 1818197Notes

Reaction equation

HRID 1818197 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d052f177181e421fadc7d4a9b2c333e5
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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