3-Benzyloxy-5-methyl-4-oxo-2-[(1,2,3,4-tetrahydro-isoquinolin-2-yl)carbonyl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine → 3-Hydroxy-5-methyl-4-oxo-2-[(1,2,3,4-tetrahydro-isoquinolin-2-yl)carbonyl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

HRID 1453859Notes

Reaction equation

HRID 1453859 reaction equation
C([O:8][C:9]1[C:10]([C:20]([N:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:23]2)=[O:21])=[N:11][N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[C:14](=[O:19])[C:13]=12)C1C=CC=CC=1>Br.CC(O)=O>[OH:8][C:9]1[C:10]([C:20]([N:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:23]2)=[O:21])=[N:11][N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[C:14](=[O:19])[C:13]=12

Participants

4

Reactant 1

HCID 689539593-Benzyloxy-5-methyl-4-oxo-2-[(1,2,3,4-tetrahydro-isoquinolin-2-yl)carbonyl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

Product 1

HCID 547246423-Hydroxy-5-methyl-4-oxo-2-[(1,2,3,4-tetrahydro-isoquinolin-2-yl)carbonyl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

3-Benzyloxy-5-methyl-4-oxo-2-[(1,2,3,4-tetrahydro-isoquinolin-2-yl)carbonyl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine (46 mg, 0.110 mmol) was dissolved in a 30% solution of HBr in AcOH, and the reaction was stirred at room temperature for 30 minutes. The solvent was removed in vacuo, and purification of the product was achieved 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 compound. 1H NMR (400 MHz, d6-DMSO) δ 9.88 (s, 1H), 7.24-7.13 (m, 4H), 5.19 (br s, 1H), 4.78 (br s, 1H), 4.37-4.34 (t, 2H), 4.20 (br s, 1H), 3.85 (br s, 1H), 3.76-3.73 (t, 2H), 2.98 (s, 3H), 2.90 (br s, 2H); ES MS (M+1)=327.

Workup

  1. customThe solvent was removed in vacuo, and purification of the product
  2. washa gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA)
  3. customCollection and concentration of the appropriate fractions

Sources & evidence

ORD record
ord-ca7423607fce4266ad6c7f40e28c1b3b
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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