Hydrochloric Acid → HCID 86649618, compound

Temperature

50 °C

A mixture of ethyl 2-(6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)-4-phenyl-1,3-thiazole-5-carboxylate (520 mg, 1.3 mmol) produced above, 1N aqueous sodium hydroxide solution (1.6 mL), ethanol (5 mL) and tetrahydrofuran (10 mL) was stirred at 50° C. for 3 hr. To the reaction mixture were added 1N hydrochloric acid (1.6 mL) and water, and the resulting precipitate was collected by filtration, washed with water and diethyl ether and dried. Ammonium chloride (346 mg, 6.5 mmol), triethylamine (0.9 mL, 6.5 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (383 mg, 2.0 mmol), 1-hydroxybenzotriazole (270 mg, 2.0 mmol) and N,N-dimethylformamide (10 mL) were added to the obtained 2-(6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid (408 mg), and the mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure, water and ethyl acetate were added to the obtained residue, and the resulting precipitate was collected by filtration, washed with water and ethyl acetate and dried. 4N Hydrogen chloride ethyl acetate solution (0.5 mL) and methanol (10 mL) were added to the obtained crude product (379 mg), and the mixture was heated, and concentrated under reduced pressure. The obtained residue was washed with methanol to give the title compound (294 mg, 56%) as a yellow solid.

1. filtrationthe resulting precipitate was collected by filtration
2. washwashed with water and diethyl ether
3. customdried
4. stirringthe mixture was stirred at room temperature for 3 days
5. concentrationThe reaction mixture was concentrated under reduced pressure, water and ethyl acetate
6. additionwere added to the obtained residue
7. filtrationthe resulting precipitate was collected by filtration
8. washwashed with water and ethyl acetate
9. customdried
10. addition4N Hydrogen chloride ethyl acetate solution (0.5 mL) and methanol (10 mL) were added to the
11. customobtained crude product (379 mg)
12. temperaturethe mixture was heated
13. concentrationconcentrated under reduced pressure
14. washThe obtained residue was washed with methanol

ORD record

ord-1baacb8c21524559aeafa8ee8abb2ea9

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139589B2