Hydrochloric Acid → HCID 18359893, compound

Temperature

80 °C

To a solution of 95 mg (0.49 mmol) of the above-obtained 7-ethoxycarbonylimidazo[5,1-b]thiazole in 10 ml of tetrahydrofuran (THF) was added 300 mg of lithium borohydride. The mixture was stirred at 80° C. (the oil bath temperature) for one hour, and then cooled. To this reaction solution, 15 ml of methanol was added little by little with ice-cooling, and the mixture was stirred at room temperature for 30 minutes. Concentrated hydrochloric acid was added to this solution little by little with ice-cooling. The resulting mixture was stirred at room temperature for one hour, and concentrated under reduced pressure. To the residue was added a 50% aqueous solution of potassium carbonate to obtain a solution, which was then extracted four times with methylene chloride. The organic layer was dried over anhydrous potassium carbonate, concentrated under reduced pressure, and purified by flash column chromatography using silica gel, eluting with a 3:17 mixture of methanol and ethyl acetate to give 30 mg (yield 40%) of 7-hydroxymethylimidazo[5,1-b]thiazole.

1. temperaturecooled
2. temperaturecooling
3. stirringthe mixture was stirred at room temperature for 30 minutes
4. temperaturecooling
5. stirringThe resulting mixture was stirred at room temperature for one hour
6. concentrationconcentrated under reduced pressure
7. additionTo the residue was added a 50% aqueous solution of potassium carbonate
8. customto obtain a solution, which
9. extractionwas then extracted four times with methylene chloride
10. dry with materialThe organic layer was dried over anhydrous potassium carbonate
11. concentrationconcentrated under reduced pressure
12. custompurified by flash column chromatography
13. washeluting with a 3:17 mixture of methanol and ethyl acetate

ORD record

ord-8c865d9e172841348b39ebf042fdd8df

Source dataset

uspto-grants-1997_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05663162