Hydrochloric Acid → 4-DesMethyl Istradefylline

HRID 1378998Notes

Reaction equation

HRID 1378998 reaction equation
[CH2:1]([N:3]1[C:12](=[O:13])[C:11]2[N:10]([CH3:14])[C:9](/[CH:15]=[CH:16]/[C:17]3[CH:22]=[CH:21][C:20]([O:23]COC)=[C:19]([O:27][CH3:28])[CH:18]=3)=[N:8][C:7]=2[N:6]([CH2:29][CH3:30])[C:4]1=[O:5])[CH3:2].Cl.[OH-].[Na+].O>O1CCCC1>[CH2:1]([N:3]1[C:12](=[O:13])[C:11]2[N:10]([CH3:14])[C:9](/[CH:15]=[CH:16]/[C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([O:27][CH3:28])[CH:18]=3)=[N:8][C:7]=2[N:6]([CH2:29][CH3:30])[C:4]1=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22908991HCID 22908991, compound

Product 1

HCID 1356653404-DesMethyl IstradefyllineYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound o (1.50 g, 3.62 mmol) obtained in Reference Example 14 was suspended in tetrahydrofuran (30 ml), and 2N HCl (9 ml) was added thereto, followed by heating under reflux for one hour. The reaction mixture was neutralized with a 2N aqueous solution of sodium hydroxide under ice-cooling, and water was added thereto. The precipitated crystals were collected by filtration and recrystallized from ethyl acetate to give 1.08 g (yield 81%) of Compound p as yellow plates.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for one hour
  3. temperaturecooling
  4. filtrationThe precipitated crystals were collected by filtration
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e0d73ba2d7634120829705e55ff1d02b
Source dataset
uspto-grants-1997_09
Patent number
US05670498

Reaction notes

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