Hydrochloric Acid → HCID 15158161, compound

HRID 466034Notes

Reaction equation

HRID 466034 reaction equation
C[O:2][C:3]([CH2:5][CH2:6][N:7]1[CH:12]=[C:11]([C:13]2[C:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:15][N:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=23)[CH:10]=[C:9]([C:28]#[N:29])[C:8]1=[O:30])=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl>C(O)C>[C:3]([CH2:5][CH2:6][N:7]1[CH:12]=[C:11]([C:13]2[C:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:15][N:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=23)[CH:10]=[C:9]([C:28]#[N:29])[C:8]1=[O:30])([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 15158157HCID 15158157, compound

Product 1

HCID 15158161HCID 15158161, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-[1-(2-methoxycarbonylethyl)-3-cyano-2-oxo-1,2-dihydropyridin-5-yl]-2-phenylpyrazolo[1,5-a]pyridine (0.46 g) and potassium carbonate (0.92 g) in 80% aqueous ethanol (4.6 ml) was stirred for 6 hours at 80° C. The mixture was acidified with 5% hydrochloric acid (pH≈2). The resultant precipitates were collected by filtration, washed with water (10 ml), and subjected to a column chromatography on silica gel (10 g) with a mixture of chloroform, methanol and acetic acid (40:4:1). The fractions containing the object compound were combined and evaporated in vacuo to give 3-[1-(2-carboxyethyl)-3-cyano-2-oxo-1,2-dihydropyridin-5-yl]-2-phenylpyrazolo[1,5-a]pyridine (0.40 g).

Workup

  1. customThe resultant precipitates
  2. filtrationwere collected by filtration
  3. washwashed with water (10 ml)
  4. additionsubjected to a column chromatography on silica gel (10 g) with a mixture of chloroform, methanol and acetic acid (40:4:1)
  5. additionThe fractions containing the object compound
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-d1e6c319a7a94919af743b30ece247fe
Source dataset
uspto-grants-1992_10
Patent number
US05155114

Reaction notes

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