Sodium Hydroxide → HCID 57515419, compound

HRID 44738Notes

Reaction equation

HRID 44738 reaction equation
[CH2:1]([O:3][CH2:4][C:5](Cl)=O)[CH3:2].[NH2:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[NH:19][CH2:20][C:21]1([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[CH:16][CH:15]=[CH:14][CH:13]=2.[OH-].[Na+]>C(O)C.O>[CH2:1]([O:3][CH2:4][C:5]1[N:19]([CH2:20][C:21]2([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:32])([CH3:31])[CH3:33])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 84189Ethoxyacetyl chlorideHCID 57457820HCID 57457820, compound

Product 1

HCID 57515419HCID 57515419, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethoxyacetyl chloride (9.00 g, 73.4 mmol) was reacted with tert-butyl 1-{[(3-aminoquinolin-4-yl)amino]methyl}cyclohexylcarbamate (27.2 g, 73.4 mmol) according to the method described in Part E of Example 9 and the resulting product was treated according to the method described in Part E of Example 9. After the solvent was removed to yield an oil, the oil was dissolved in ethanol (300 mL) and water (30 mL). Sodium hydroxide (4.3 g, 108 mmol) was added and the solution was heated at reflux for 6 h. The volatiles were removed under reduced pressure and the resulting brown oil was partitioned between dichloromethane (500 mL) and water. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to yield a brown oil. Purification by flash chromatography (silica gel, 30% ethyl acetate/hexanes) provided tert-butyl 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexylcarbamate as a brown solid (11.9 g, 38%).

Workup

  1. additionthe resulting product was treated
  2. customAfter the solvent was removed
  3. customto yield an oil
  4. temperaturethe solution was heated
  5. temperatureat reflux for 6 h
  6. customThe volatiles were removed under reduced pressure
  7. customthe resulting brown oil was partitioned between dichloromethane (500 mL) and water
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto yield a brown oil
  12. customPurification by flash chromatography (silica gel, 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-5ca3e6e6beaf49248aca349253710033
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

Loading…