Ammonia → 3-[2,6-Dimethyl-3,5-bis(methoxycarbonyl)-1,4-dihydropyridin-4-yl]-2-phenylpyrazolo[1,5-a]pyridine

HRID 466036Notes

Reaction equation

HRID 466036 reaction equation
[C:1]1([C:7]2[C:15]([CH:16]=O)=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]([O:24][CH3:25])(=[O:23])[CH2:19][C:20]([CH3:22])=O.[NH3:26]>CO.C(Cl)(Cl)Cl>[CH3:22][C:20]1[NH:26][C:20]([CH3:22])=[C:19]([C:18]([O:24][CH3:25])=[O:23])[CH:16]([C:15]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:8][N:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=23)[C:19]=1[C:18]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 7757Methyl acetoacetateHCID 151581792-Phenylpyrazolo[1,5-a]pyridine-3-carbaldehyde

Product 1

HCID 151581633-[2,6-Dimethyl-3,5-bis(methoxycarbonyl)-1,4-dihydropyridin-4-yl]-2-phenylpyrazolo[1,5-a]pyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 2-phenylpyrazolo[1,5-a]pyridine-3-carbaldehyde (1.00 g), methyl acetoacetate (1.10 g), and 14% methanolic ammonia (18 ml) in a mixture of methanol (20 ml) and chloroform (10 ml) was stirred for 246 hours at room temperature. The solvent was removed in vacuo and the residue was dissolved in methylene chloride (30 ml). The solution was washed with water (10 ml) and sodium chloride aqueous solution (10 ml), dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (15 g) with a mixture of n-hexane and ethyl acetate (2:1). The fractions containing the object compound were combined and evaporated in vacuo to give 3-[2,6-dimethyl-3,5-bis(methoxycarbonyl)-1,4-dihydropyridin-4-yl]-2-phenylpyrazolo[1,5-a]pyridine. This compound was purified from a mixture of ethyl acetate and n-hexane.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in methylene chloride (30 ml)
  3. washThe solution was washed with water (10 ml) and sodium chloride aqueous solution (10 ml)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel (15 g) with a mixture of n-hexane and ethyl acetate (2:1)
  7. additionThe fractions containing the object compound
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-8c585f039fc24d2b9df6df1e17a32d11
Source dataset
uspto-grants-1992_10
Patent number
US05155114

Reaction notes

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