Hydrochloric Acid → HCID 54066728, compound

HRID 1977915Notes

Reaction equation

HRID 1977915 reaction equation
C(C([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]2[N:21]=[C:20]([C:22]3[CH:26]=C(C)N[C:23]=3[CH3:28])[CH:19]=[CH:18][CH:17]=2)[CH:11]=1)(CC#N)C([O-])=O)C.Cl.[CH:30]([O-:32])=O.[NH4+:33]>[Pd].C(O)C>[CH3:14][C:13]1[NH:33][C:10]([CH3:15])=[CH:11][C:12]=1[C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([C:22]2[CH:23]=[CH:28][C:17]([CH:18]3[CH2:19][CH2:20][NH:21][C:30]3=[O:32])=[CH:16][CH:26]=2)[N:21]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2723923Ammonium formate2×HCID 86585577HCID 86585577, compound

Product 1

HCID 54066728HCID 54066728, compoundYield 16.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a 125 mL round-bottomed flask equipped with condenser and N2 inlet were added 2.84 g (7.61 mmol) ethyl-3-[2-(2,5-dimethylpyrrolyl)-6-pyridyl]phenyl-3-cyano-propionate, 50 mL ethanol, and 1 mL concentrated hydrochloric acid. The solution was heated as 700 mg 10% palladium-on-carbon and 2.4 g (38.07 mmol) ammonium formate were added, and the reaction heated at 80° C. for 4.75 hours, with additional catalyst and ammonium formate at 1 hour intervals. The reaction was cooled and filtered through Celite, and the filtrate evaporated. The residue was taken up in ethyl acetate, washed with aqueous sodium hydroxide, dried over sodium sulfate, and evaporated. The residue was taken up in 50 mL dry toluene, treated with 5 mL triethylamine, and heated at reflux for 1 hour. The reaction was then cooled, washed with dilute aqueous hydrochloric acid and brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using methylene chloride/methanol as eluant to afford 204.5 mg (8.1%) of an oil.

Workup

  1. customTo a 125 mL round-bottomed flask equipped with condenser and N2 inlet
  2. additionwere added
  3. temperatureThe reaction was cooled
  4. filtrationfiltered through Celite
  5. customthe filtrate evaporated
  6. washwashed with aqueous sodium hydroxide
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. additiontreated with 5 mL triethylamine
  10. temperatureheated
  11. temperatureat reflux for 1 hour
  12. temperatureThe reaction was then cooled
  13. washwashed with dilute aqueous hydrochloric acid and brine
  14. dry with materialdried over sodium sulfate
  15. customevaporated
  16. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-38609b60906c4620a4b96794f6b7e83d
Source dataset
uspto-grants-2001_05
Patent number
US06235750B1

Reaction notes

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