Hydrochloric Acid → HCID 178515830, compound

HRID 965369Notes

Reaction equation

HRID 965369 reaction equation
[C:1]([CH2:3][C:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=1[N:10]1[C:15](=[O:16])[CH:14]=[CH:13][C:12]([C:17]2[C:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:19][N:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=23)=[N:11]1)#[N:2].[N-:32]=[N+:33]=[N-:34].[Na+].[Cl-].[NH4+].Cl>CN1CCCC1=O.O>[NH:32]1[C:1]([CH:3]=[C:4]2[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]2[N:10]2[C:15](=[O:16])[CH:14]=[CH:13][C:12]([C:17]3[C:18]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)=[N:19][N:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=34)=[N:11]2)=[N:2][N:34]=[N:33]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 22629194HCID 22629194, compound

Product 1

HCID 178515830HCID 178515830, compoundYield 7.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 3-[2-(2-cyanomethyl-1-cyclohexenyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]-pyridine (1 g), sodium azide (480 mg) and ammonium chloride (200 mg) in 1-methyl-2-pyrrolidone (10 ml) was heated at 140° to 150° C. for 6 hours with stirring. The reaction mixture was cooled to room temperature, which was poured into water and adjusted to pH 1.0 with 1N-aqueous hydrochloric acid. The resulting solution was extracted three times with ethyl acetate (100 ml). Organic layers were combined, washed with brine (50 ml×2) and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel eluting in turn with 2%, 3%, 5%, 10% methanol in dichloromethane. Fractions containing desired product were collected. Evaporation of the solvent gave a residue which was recrystallized from ethyl acetate to give 3-[2-{2-(1H-tetrazol-5-yl)methylenecyclohexyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (85 mg).

Workup

  1. temperaturewas heated at 140° to 150° C. for 6 hours
  2. extractionThe resulting solution was extracted three times with ethyl acetate (100 ml)
  3. washwashed with brine (50 ml×2)
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent
  6. customgave a residue, which
  7. customwas chromatographed on silica gel eluting in turn with 2%, 3%, 5%, 10% methanol in dichloromethane
  8. additionFractions containing desired product
  9. customwere collected
  10. customEvaporation of the solvent
  11. customgave a residue which
  12. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-7a6f3eb613aa46fd982893042d0442e9
Source dataset
uspto-grants-1998_06
Patent number
US05773530

Reaction notes

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