Water → HCID 57438746, compound

HRID 2233083Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([C:16]([O:18]C)=[O:17])=[N:14][CH:13]=[CH:12][N:11]3[CH:20]=2)=[CH:4][CH:3]=1.O.O.[OH-].[Li+]>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([C:16]([OH:18])=[O:17])=[N:14][CH:13]=[CH:12][N:11]3[CH:20]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

The crude methyl 2-(4-fluorophenyl)imidazo[1,2-a]pyrazine-8-carboxylate (35.7 g, 65.8 mmol) was dissolved in 1,4-dioxane (200 mL), then water (20.2 mL) and lithium hydroxide monohydrate (27.6 g, 658 mmol) were added. Heated to about 50° C. overnight. The reaction mixture was cooled to ambient temperature, filtered, and the collected solid was washed with Et2O (4×70 mL). The resulting brown solid was suspended in water (200 mL) and the pH was adjusted to ˜5 with glacial HOAc (100 mL). The solid was collected, washed with water (4×75 mL) and Et2O (2×80 mL) to give the wet crude title compound (26.4 g, 156%) that was carried on without further purification. LC/MS (Table 1, Method b) Rt=1.21 min; MS m/z: 258.2 (M+H)+.

Workup

temperatureThe reaction mixture was cooled to ambient temperature
filtrationfiltered
washthe collected solid was washed with Et2O (4×70 mL)
customThe solid was collected
washwashed with water (4×75 mL) and Et2O (2×80 mL)

Sources & evidence

ORD record: ord-a8f2123c4c9f49bc8fb9783f3b6101c3
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709468B2

Reaction notes

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