Ethanol → HCID 57447013, compound

A solution of ethoxyacetyl chloride (7.00 g, 57.1 mmol) in dichloromethane (10 mL) was added dropwise to a stirred solution of ethyl 4-(3-aminoquinolin-4-ylamino)butyrate (prepared as described in Steps 1-2 of Example 17, 12.5 g, 45.7 mmol) in dichloromethane (100 mL) at room temperature. After 1.5 hours, the reaction mixture was concentrated under reduced pressure to afford a solid to which was added ethanol (100 mL) and triethylamine (17.4 mL, 125 mmol). The solution was left at room temperature for 5 days, then was heated at reflux for 2 hours. The solution was concentrated under reduced pressure. The residue was partitioned between dichloromethane (150 mL) and water (50 mL). The organic layer was washed with water (50 mL) and saturated aqueous sodium bicarbonate (50 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure to yield 15.4 g of ethyl 4-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butanoate as a brown oil that was used in the next step without purification.

1. concentrationthe reaction mixture was concentrated under reduced pressure
2. customto afford a solid to which
3. waitThe solution was left at room temperature for 5 days
4. temperaturewas heated
5. temperatureat reflux for 2 hours
6. concentrationThe solution was concentrated under reduced pressure
7. customThe residue was partitioned between dichloromethane (150 mL) and water (50 mL)
8. washThe organic layer was washed with water (50 mL) and saturated aqueous sodium bicarbonate (50 mL)
9. dry with materialdried over potassium carbonate
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure

ORD record

ord-95ba999ca19c405e981c8c029566e4e6

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691837B2