Trimethyl orthovalerate → HCID 22381772, compound

HRID 895788Notes

Reaction equation

HRID 895788 reaction equation
CO[C:3](OC)(OC)[CH2:4][CH2:5][CH2:6][CH3:7].[NH2:12][C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:22]=1[NH:23][CH2:24][CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:20][CH:19]=[CH:18][CH:17]=2>C1(C)C=CC=CC=1>[CH2:4]([C:3]1[N:23]([CH2:24][CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:32])[CH3:31])[C:22]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:12]=1)[CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 83755Trimethyl orthovalerateHCID 12016824tert-Butyl 2-(3-aminoquinolin-4-ylamino)ethylcarbamate

Product 1

HCID 22381772HCID 22381772, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trimethylorthovalerate (5.9 g, 36.4 mmol) was added with stirring to a solution of 1,1-dimethylethyl N-{2-[(3-aminoquinolin-4-yl)amino]ethyl}carbamate (10.0 g, 33.1 mmol) in anhydrous toluene (100 mL). The reaction mixture was heated to reflux. A 10 mL portion of toluene was removed using a Dean Stark trap and the reaction mixture was maintained for 36 hours. An additional 40 mL of toluene was removed and then the reaction was allowed to cool to ambient temperature with continued stirring. The resulting precipitate was isolated by filtration and dried to provide 6.2 g of 1,1-dimethylethyl N-[2-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]carbamate as a tan solid. Thin layer chromatography (silica gel; 10% methanol in dichloromethane) analysis indicated that the material was pure.

Workup

  1. temperatureThe reaction mixture was heated to reflux
  2. customA 10 mL portion of toluene was removed
  3. temperaturethe reaction mixture was maintained for 36 hours
  4. customAn additional 40 mL of toluene was removed
  5. customThe resulting precipitate was isolated by filtration
  6. customdried

Sources & evidence

ORD record
ord-527114138380446f9ba83b430ccd15b5
Source dataset
uspto-grants-2005_07
Patent number
US06916925B1

Reaction notes

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