Hydrochloric Acid → 5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)-1-(pyridin-2-yl)pyridazin-4(1H)-one

HRID 1528079Notes

Reaction equation

HRID 1528079 reaction equation
[CH3:1][O:2][C:3]1[C:4]([OH:20])=[C:5]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)[N:6]=[N:7][CH:8]=1.F[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN1C(=O)CCC1>[CH3:1][O:2][C:3]1[C:4](=[O:20])[C:5]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)=[N:6][N:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 97462-FluoropyridineHCID 10796Cesium carbonateHCID 178493808HCID 178493808, compound

Product 1

HCID 866865615-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)-1-(pyridin-2-yl)pyridazin-4(1H)-oneYield 25.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4-ol (60 mg), 2-fluoropyridine (65 mg) and cesium carbonate (364 mg) in NMP (2 mL) was stirred at 100° C. for 3 days, 1M hydrochloric acid was added thereto, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate/methanol) to give the title compound (20 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-5243a3ae28b240659bf7c1b64f518cb8
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

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