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-Eintrag

ord-140edaebe7f94c17897578c5b3632cb9

Quelldatensatz

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07491720B2