Potassium Hydroxide → HCID 67196000, compound

HRID 1423023Notes

Reaction equation

HRID 1423023 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[N:8]([C:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[N:13][CH:14]=2)[CH:9]=[CH:10][N:11]=1)=[O:5])C.[OH-].[K+]>CO.O>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[N:8]3[CH:9]=[CH:10][N:11]=[C:6]([C:4]([OH:5])=[O:3])[C:7]3=[CH:14][N:13]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67196418HCID 67196418, compound

Product 1

HCID 67196000HCID 67196000, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 3-(4-fluorophenyl)-imidazo[1,5-a]pyrazine-8-carboxylic acid ethyl ester (440.0 mg, 1.54 mmol) in methanol (10 mL) is added in several portions a solution of 85% KOH (330 mg, 4.9 mmol) in water (3 mL) (additional water is added to suspend the solid that precipitated) and the mixture is warmed at reflux. The methanol is removed in vacuo and the residue is diluted with water (15 mL) and made acidic (pH=4) with 1 N aqueous HCl. The solid is collected by filtration washing with water and then ether to afford 3-(4-fluorophenyl)-imidazo[1,5-a]pyrazine-8-carboxylic acid.

Workup

  1. additionis added
  2. customthat precipitated) and the mixture
  3. temperatureis warmed
  4. temperatureat reflux
  5. customThe methanol is removed in vacuo
  6. additionthe residue is diluted with water (15 mL)
  7. filtrationThe solid is collected by filtration
  8. washwashing with water

Sources & evidence

ORD record
ord-2b14808ff97e4272aef2201bcb5547aa
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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