Hydrochloric Acid → HCID 178505586, compound

HRID 1792527Notes

Reaction equation

HRID 1792527 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([C:19]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=5)=[CH:20][N:21]=4)[CH:18]=3)=[CH:11][N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:9]=2)=[CH:4][CH:3]=1.Cl.O1CCCC1.[OH-].[Na+]>O.C(OCC)(=O)C.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([C:19]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=5)=[CH:20][N:21]=4)[CH:18]=3)=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22032558HCID 22032558, compound

Product 1

HCID 178505586HCID 178505586, compoundYield 44.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

147 mg 6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-3-(2-pyridyl)imidazo[1,2-a]pyridine obtained in Example 22, 1.8 mL of 5 N hydrochloric acid, 4 ml tetrahydrofuran and 4 mL methanol were stirred overnight at room temperature. The reaction solution was cooled and then basified with 5 N aqueous sodium hydroxide, followed by adding ethyl acetate and water to separate an organic layer. The organic layer was washed with water and brine and dried over anhydrous sodium sulfate. The drying agent was filtered off, the filtrate was evaporated, the residue was triturated with dichloromethane, and the crystals were separated by filtration. This product was dried under vacuum to give 39 mg of the title compound as colorless crystals.

Workup

  1. temperatureThe reaction solution was cooled
  2. customto separate an organic layer
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe filtrate was evaporated
  7. customthe residue was triturated with dichloromethane
  8. customthe crystals were separated by filtration
  9. customThis product was dried under vacuum

Sources & evidence

ORD record
ord-081d62b82af24a3a9c58599dd0049bb0
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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