Trimethyl orthovalerate → 6-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)-1-phenylhexan-1-one

HRID 521272Notes

Reaction equation

HRID 521272 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:26](OC)(OC)(OC)[CH2:27][CH2:28][CH2:29][CH3:30]>C1(C)C=CC=CC=1>[CH2:27]([C:26]1[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 83755Trimethyl orthovalerateHCID 689281276-(3-Aminoquinolin-4-ylamino)-1-phenylhexan-1-one

Product 1

HCID 689304156-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)-1-phenylhexan-1-oneYield 87.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 6-(3-aminoquinolin-4-ylamino)-1-phenylhexan-1-one (2.09 g, 6.25 mmol) and trimethyl orthovalerate (1.52 g, 9.37 mmol) in toluene (50 mL) was heated at reflux under a Dean-Stark trap for 2 hours, then concentrated under reduced pressure to provide 6-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)-1-phenylhexan-1-one (2.19 g) as a dark red oil that was used directly in the next step without further purification.

Workup

  1. temperatureat reflux under a Dean-Stark trap for 2 hours
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a19f6c1e13c34c5bb01a90967235a099
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

Loading…