Trifluoroacetic acid → HCID 68954184, compound

HRID 1453847Notes

Reaction equation

HRID 1453847 reaction equation
C([O:8][C:9]1[C:10]([C:21]([O:23][CH3:24])=[O:22])=[N:11][N:12]2[C:17]([CH3:18])=[CH:16][N:15]([CH3:19])[C:14](=[O:20])[C:13]=12)C1C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)(Cl)Cl>[OH:8][C:9]1[C:10]([C:21]([O:23][CH3:24])=[O:22])=[N:11][N:12]2[C:17]([CH3:18])=[CH:16][N:15]([CH3:19])[C:14](=[O:20])[C:13]=12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 68949949HCID 68949949, compound

Product 1

HCID 68954184HCID 68954184, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of methyl 3-benzyloxy-5,7-dimethyl-4-oxo-4,5-dihydropyrazolo[1,5-a]pyrazine-2-carboxylate (62 mg, 0.189 mmol) in CHCl3 was added TFA (200 μL), and the reaction was stirred at room temperature for 2 hours. Following treatment with additional TFA (200 μL), the reaction was heated to 50° C. overnight. The solvent was removed in vacuo, and the resulting residue was purified by reverse phase chromatography on a C-18 column using a gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA). Collection and concentration of the appropriate fractions afforded the title product as a white solid. 1H NMR (400 MHz, d6-DMSO) δ 6.44 (s, 1H), 4.03 (s, 3H), 3.48 (s, 3H), 2.44 (s, 3H); ES MS (M+Na)=260.

Workup

  1. temperaturethe reaction was heated to 50° C. overnight
  2. customThe solvent was removed in vacuo
  3. customthe resulting residue was purified by reverse phase chromatography on a C-18 column
  4. washa gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA)
  5. customCollection and concentration of the appropriate fractions

Sources & evidence

ORD record
ord-2f748a51cc164e54b2953ab685d5f871
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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