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

HRID 2362515Notes

Reaction equation

HRID 2362515 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.[CH:26](OC)(OC)OC.Cl.N1C=CC=CC=1>C1(C)C=CC=CC=1>[N:12]1([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]=[CH:26]1

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 10176127Pyridinium chlorideHCID 689281276-(3-Aminoquinolin-4-ylamino)-1-phenylhexan-1-one

Product 1

HCID 689325036-(1H-imidazo[4,5-c]quinolin-1-yl)-1-phenylhexan-1-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

By the general method described in Step 6 of Example 4, a solution of 6-(3-aminoquinolin-4-ylamino)-1-phenylhexan-1-one (2.76 g, 8.25 mmol), trimethyl orthoformate (1.5 g, 9.9 mmol), and pyridine hydrochloride (95 mg, 0.83 mmol) in toluene (26 mL) was heated at reflux under a Dean-Stark trap for 2 hours, then concentrated under reduced pressure to provide 6-(1H-imidazo[4,5-c]quinolin-1-yl)-1-phenylhexan-1-one as a dark 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-ed8b126afd4c4b3c86d183d5c29c3a11
Source dataset
uspto-grants-2014_04
Patent number
US08691837B2

Reaction notes

Loading…