Hydrochloric Acid → 2-(4-Fluorophenyl)imidazo[1,2-a]pyrazine

HRID 2233075Notes

Reaction equation

HRID 2233075 reaction equation
COC([C:5]1[C:6]2[N:7]([CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[N:13]=2)[CH:8]=[CH:9][N:10]=1)=O.Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[F:20][C:17]1[CH:16]=[CH:15][C:14]([C:12]2[N:13]=[C:6]3[CH:5]=[N:10][CH:9]=[CH:8][N:7]3[CH:11]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 57438736HCID 57438736, compound

Product 1

HCID 32311372-(4-Fluorophenyl)imidazo[1,2-a]pyrazineYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
105 °C

Procedure

A mixture of 2-(4-fluorophenyl)imidazo[1,2-a]pyrazine-8-carboxylic acid methyl ester (Preparation #1, 6.30 g, 23.2 mmol) in DCM (66 mL) was treated with 1.0 M HCl in water (200 mL). The mixture was heated at about 105° C. open to the air for about 16 h. The solution was allowed to cool and was treated with saturated aqueous NaHCO3 and DCM. The mixture was sonicated to dissolve all solids and the layers were separated. The aqueous layer was washed with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to yield the title compound (4.60 g, 93%): LC/MS (Table 1, Method b) Rt=1.6 min; MS m/z: 214.3 (M+H)+.

Workup

  1. temperatureto cool
  2. customThe mixture was sonicated
  3. dissolutionto dissolve all solids
  4. customthe layers were separated
  5. washThe aqueous layer was washed with EtOAc
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee450fa9cc234bc6ae9be034dd1711de
Source dataset
uspto-grants-2010_05
Patent number
US07709468B2

Reaction notes

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