Hydrochloric Acid → 3-[2-{2-(2-Hydroxyethyl)-1-cyclohexenyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

HRID 965364Notes

Reaction equation

HRID 965364 reaction equation
[C:1]([CH2:4][C:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=1[N:11]1[C:16](=[O:17])[CH:15]=[CH:14][C:13]([C:18]2[C:19]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:20][N:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=23)=[N:12]1)(O)=[O:2].Cl>O1CCCC1>[OH:2][CH2:1][CH2:4][C:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=1[N:11]1[C:16](=[O:17])[CH:15]=[CH:14][C:13]([C:18]2[C:19]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:20][N:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=23)=[N:12]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9910335FR-166124

Product 1

HCID 226292383-[2-{2-(2-Hydroxyethyl)-1-cyclohexenyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridineYield 56.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-[2-(2-carboxymethyl-1-cyclohexenyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (2.07 g) in tetrahydrofuran (40 ml) was added dropwise under nitrogen atmosphere a solution of borane-tetrahydrofuran complex in tetrahydrofuran (1M solution, 9.72 ml) at -10° C. over a period of 10 minutes. The reaction mixture was allowed to stir at room temperature for 5.5 hours. Then, the mixture was cooled to 10° C. in an ice bath and treated with 1N hydrochloric acid. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined extracts were washed with 1N aqueous sodium hydroxide solution, water, and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The crude material was purified by column chromatography on silica gel (toluene:MeOH=10:1) to give colorless crystals of 3-[2-{2-(2-hydroxyethyl)-1-cyclohexenyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (1.14 g).

Workup

  1. temperatureThen, the mixture was cooled to 10° C. in an ice bath
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane
  4. washThe combined extracts were washed with 1N aqueous sodium hydroxide solution, water, and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by column chromatography on silica gel (toluene:MeOH=10:1)

Sources & evidence

ORD record
ord-af9595f8e5124b17854dbd7282e635ab
Source dataset
uspto-grants-1998_06
Patent number
US05773530

Reaction notes

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