Hydrochloric Acid → HCID 57441067, compound

HRID 1664068Notes

Reaction equation

[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][C:6]([O:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[C:14]([O:16]C)=[O:15])=[N:5]2.[OH-].[Na+].Cl>CO>[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][C:6]([O:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[C:14]([OH:16])=[O:15])=[N:5]2

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 3-(imidazo[1,2-b]pyridazin-6-yloxy)benzoate (1665 mg, 6.18 mmol) in methanol (30 mL) was added 8N aqueous sodium hydroxide solution (3.00 mL), and the mixture was stirred at room temperature for 18 hr and at 80° C. for 8 hr. After the reaction mixture was allowed to cool to room temperature, 6N hydrochloric acid (4.00 mL) was added to the mixture, and the mixture was concentrated under reduced pressure. Water (30 mL) was added to the residue, and the precipitate was collected by filtration and washed with water. The precipitate was suspended in methanol (10 mL) and the suspension was stirred with heating under reflux for 10 min. After the suspension was allowed to cool to room temperature, the precipitate was collected by filtration washed with methanol and dried under reduced pressure to give the title compound (1045 mg, 4.09 mmol, yield 66%) as a white solid.

Workup

temperatureto cool to room temperature
concentrationthe mixture was concentrated under reduced pressure
additionWater (30 mL) was added to the residue
filtrationthe precipitate was collected by filtration
washwashed with water
stirringthe suspension was stirred
temperaturewith heating
temperatureunder reflux for 10 min
temperatureto cool to room temperature
filtrationthe precipitate was collected by filtration
washwashed with methanol
customdried under reduced pressure

Sources & evidence

ORD record: ord-a64cac293fc74c1b8a7a67529b306fe6
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08034812B2

Reaction notes

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