Methoxyacetyl chloride → HCID 67051018, compound

HRID 598350Notes

Reaction equation

HRID 598350 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([NH2:19])=[C:12]2[NH:20][CH2:21][CH:22]([CH3:24])[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][O:26][CH2:27][C:28](Cl)=O>ClCCl>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[CH:14][C:13]3[N:19]=[C:28]([CH2:27][O:26][CH3:25])[N:20]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 67050972HCID 67050972, compound

Product 1

HCID 67051018HCID 67051018, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6-Benzyloxy-N4-(2-methylpropyl)quinoline-3,4-diamine was dissolved in 200 mL of dichloromethane and methoxyacetyl chloride (1.85 g, 17.1 mmol), diluted in 10 mL of dichloromethane, was added dropwise. After 1 hour, the solvent was removed and the resulting solid was dissolved in 250 mL of 3:1 methanol:water. Aqueous potassium carbonate (6M) was added and the reaction was heated at reflux temperature for 3 hours. The solvent was removed and the residue was partitioned between 200 mL of dichloromethane and 100 mL of water. The aqueous fraction was isolated and extracted three times with dichloromethane. The combined organic fractions were dried, filtered, and concentrated under reduced pressure. The resulting material was purified by flash column chromatography on silica gel eluting with a gradient of 0-4% methanol in dichloromethane. The clean fractions were combined and concentrated to give 4.2 g of 8-benzyloxy-1-(2-methylpropyl)-2-methoxymethyl-1H-imidazo[4,5-c]quinoline as a light brown solid.

Workup

  1. additionwas added dropwise
  2. customthe solvent was removed
  3. dissolutionthe resulting solid was dissolved in 250 mL of 3:1 methanol
  4. additionAqueous potassium carbonate (6M) was added
  5. temperaturethe reaction was heated
  6. temperatureat reflux temperature for 3 hours
  7. customThe solvent was removed
  8. customthe residue was partitioned between 200 mL of dichloromethane and 100 mL of water
  9. customThe aqueous fraction was isolated
  10. extractionextracted three times with dichloromethane
  11. customThe combined organic fractions were dried
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customThe resulting material was purified by flash column chromatography on silica gel eluting with a gradient of 0-4% methanol in dichloromethane
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-509f82186c7d428d9d921e239ebc4cc5
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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