Trimethyl orthoacetate → HCID 21936603, compound

HRID 432741Notes

Reaction equation

HRID 432741 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][O:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:26](OC)(OC)(OC)[CH3:27].Cl.[NH+]1C=CC=CC=1>ClCCCl>[CH3:26][C:27]1[N:12]([CH2:13][CH2:14][O:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])[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

Participants

5

Reactant 3

HCID 15050Trimethyl orthoacetateHCID 12106200Tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy)ethylcarbamateHCID 21584435Pyridinium hydrochloride

Product 1

HCID 21936603HCID 21936603, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy}ethylcarbamate (12.05 g, 34.8 mmol) in 200 mL of 1,2-dichloroethane was treated with trimethyl orthoacetate (5.50 mL, 43.2 mmol) and the reaction mixture was heated to reflux. A 100 mg portion of pyridinium hydrochloride was then added and refluxing was continued for 4 h. The reaction was then cooled and washed with water and brine. The organic portion was dried over Na2SO4 and concentrated to give an orange foam. The foam was triturated with ether and filtered to yield 10.76 g of tert-butyl 2-[2-(2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate as a tan solid.

Workup

  1. temperaturethe reaction mixture was heated to reflux
  2. temperaturerefluxing
  3. temperatureThe reaction was then cooled
  4. washwashed with water and brine
  5. dry with materialThe organic portion was dried over Na2SO4
  6. concentrationconcentrated
  7. customto give an orange foam
  8. customThe foam was triturated with ether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-cc66143d620d4cff92f9bb009a047acd
Source dataset
uspto-grants-2003_12
Patent number
US06664265B2

Reaction notes

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