Hydrochloric Acid → HCID 178432915, compound

HRID 245768Notes

Reaction equation

HRID 245768 reaction equation
C([O:4][C@H:5]1[CH2:10][CH2:9][C@@H:8]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19]([CH3:20])[C:14]3=[C:13]([Br:21])[N:12]=2)[CH2:7][CH2:6]1)(=O)C.[OH-].[K+].Cl>C(#N)C.O>[Br:21][C:13]1[N:12]=[C:11]([C@@H:8]2[CH2:9][CH2:10][C@H:5]([OH:4])[CH2:6][CH2:7]2)[N:15]2[CH:16]=[CH:17][N:18]=[C:19]([CH3:20])[C:14]=12

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 178476585HCID 178476585, compound

Product 1

HCID 178432915HCID 178432915, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A solution of (cis)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl acetate (43.6 mmol, 15.34 g) in acetonitrile (40 ml) was added potassium hydroxide (218 mmol, 12.22 g) in water (40 ml) and the mixture was stirred at 100° C. overnight. Then the reaction mixture was cooled to room temperature, acidified with 2N hydrochloric acid and extracted with dichloromethane twice. The combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo to give (cis)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexanol (9.37 g).

Workup

  1. temperatureThen the reaction mixture was cooled to room temperature
  2. extractionextracted with dichloromethane twice
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-207dd66ecc3f43ac9a05117b785056b2
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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