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

HRID 1818134Notes

Reaction equation

HRID 1818134 reaction equation
[C:1](OCC)(OCC)(OCC)[CH2:2][CH3:3].[NH2:13][C:14]1[CH:15]=[N:16][C:17]2[C:22]([C:23]=1[NH:24][CH2:25][C:26]([CH3:29])([OH:28])[CH3:27])=[CH:21][CH:20]=[C:19]([Br:30])[CH:18]=2>C1(C)C=CC=CC=1.Cl.N1C=CC=CC=1>[Br:30][C:19]1[CH:20]=[CH:21][C:22]2[C:23]3[N:24]([CH2:25][C:26]([CH3:27])([OH:28])[CH3:29])[C:1]([CH2:2][CH3:3])=[N:13][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1

Participants

5

Reactant 2

HCID 66995Ethyl orthopropionateHCID 219844571-(3-Amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol

Product 1

HCID 219842201-(7-bromo-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-olYield 74.9%

Reagents, catalysts & solvents 2

HCID 10176127Pyridinium chlorideCatalystHCID 1140TolueneSolvent

Procedure

Triethyl orthopropionate (12.9 g, 73.2 mmol) and pyridine hydrochloride (220 mg) were added to a solution of 1-(3-amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol (22.1 g, 70.6 mmol) in anhydrous toluene (300 mL), and the reaction was heated at reflux for three hours. The reaction was allowed to cool to ambient temperature and stand overnight; a precipitate formed. The precipitate was isolated by filtration, washed with toluene, and air-dried to provide 18.42 g of 1-(7-bromo-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol as beige crystals.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for three hours
  3. customa precipitate formed
  4. customThe precipitate was isolated by filtration
  5. washwashed with toluene
  6. customair-dried

Sources & evidence

ORD record
ord-66dccb099fa94db1a5093b24b68fb564
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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