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

HRID 9384

Reaction equation

HRID 9384 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-02ae989cd742463bb79e291df0179b6e
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Linked notes

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