Tetrahydrofuran → Methyl 4-bromo-6-(2-thiazolylamino)-2-pyridinecarboxylate

To a mixture of 2.37 g of methyl 6-(3-benzoylthioureido)-4-bromopyridine-2-carboxylate, 20 ml of tetrahydrofuran and 40 ml of methanol was added 673 mg of potassium hydroxide. The reaction mixture was stirred at room temperature for 1.5 hours, and acidified with a hydrochloric acid-methanol solution. The solvents were concentrated in vacuo. The resulting residue was dissolved in 60 ml of 1,4-dioxane and 3.53 ml of a 40% chloroacetaldehyde aqueous solution was added thereto. After the reaction mixture was heated under reflux for 1 hour, 40 ml of a hydrochloric acid-methanol solution and 60 ml of methanol were added thereto at room temperature, and the resulting mixture was stirred overnight. The reaction mixture was concentrated in vacuo and the residue was recrystallized from methanol-diethyl ether to give the title compound.

1. concentrationThe solvents were concentrated in vacuo
2. dissolutionThe resulting residue was dissolved in 60 ml of 1,4-dioxane
3. addition3.53 ml of a 40% chloroacetaldehyde aqueous solution was added
4. temperatureAfter the reaction mixture was heated
5. temperatureunder reflux for 1 hour
6. addition40 ml of a hydrochloric acid-methanol solution and 60 ml of methanol were added
7. stirringat room temperature, and the resulting mixture was stirred overnight
8. concentrationThe reaction mixture was concentrated in vacuo
9. customthe residue was recrystallized from methanol-diethyl ether

ORD record

ord-b50b56df81264a5097ce1837e760b028

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07834018B2