Hydrochloric Acid → Pirmagrel

HRID 326146Notes

Reaction equation

HRID 326146 reaction equation
C([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[N:16]2[CH:17]=[N:18][CH:19]=[C:15]2[CH:14]=[CH:13][CH:12]=1)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[N:16]2[CH:17]=[N:18][CH:19]=[C:15]2[CH:14]=[CH:13][CH:12]=1)([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 132061385-(5-Ethoxycarbonylpentyl)imidazo[1,5-a]pyridine

Product 1

HCID 55390Pirmagrel

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(5-Ethoxycarbonylpentyl)-imidazo[1,5-a]pyridine (1091 g) is charged into a 12 liter round bottom flask under a nitrogen atmosphere. Ethyl alcohol (95%, 420 ml) is added while stirring. With continued stirring, 2 N NaOH (2100 ml) is added in portions. After complete addition the mixture is warmed at 70° for 20 minutes, at which time a solution is obtained, and heating is continued for 2 hours. Additional sodium hydroxide (50% solution, 21 ml) is added and heating is continued for 40 more minutes. The reaction mixture is cooled, 12 N HCl (30 ml) is added, and the ethyl alcohol is partially removed by evaporation under reduced pressure. The resulting solution is washed with ethyl ether (1700 ml), decolorized with charcoal, filtered, and acidified with acetic acid (300 ml). The product that crystallizes at 4° overnight is collected, washed first with water, then with ethyl ether (1000 ml), and dried to give 5-(5-carboxypentyl)-imidazo[1,5-a]pyridine, melting at 146°-8°, and identical to the product of Example 2.

Workup

  1. stirringWith continued stirring
  2. additionAfter complete addition the mixture
  3. temperatureis warmed at 70° for 20 minutes, at which time a solution
  4. customis obtained
  5. temperatureheating
  6. temperatureheating
  7. temperatureThe reaction mixture is cooled
  8. customthe ethyl alcohol is partially removed by evaporation under reduced pressure
  9. washThe resulting solution is washed with ethyl ether (1700 ml)
  10. filtrationfiltered
  11. customThe product that crystallizes at 4° overnight
  12. customis collected
  13. washwashed first with water
  14. dry with materialwith ethyl ether (1000 ml), and dried

Sources & evidence

ORD record
ord-b4357ba187bc42bfae2a98ec769d0c60
Source dataset
uspto-grants-1984_04
Patent number
US04444775

Reaction notes

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