Hydrochloric Acid → HCID 178515830, compound

HRID 276957Notes

Reaction equation

HRID 276957 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

Conditions

Temperature
145 °C

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. temperatureThe reaction mixture was cooled to room temperature
  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-a308c24f9f804ac2b9b45f9b103b3d4e
Source dataset
uspto-grants-2002_03
Patent number
US06355640B1

Reaction notes

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