Methyl 3-benzyloxy-5-(4-fluorobenzyl)-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate → HCID 54722069, compound

HRID 1453823Notes

Reaction equation

HRID 1453823 reaction equation
C([O:8][C:9]1[C:10]([C:27]([O:29][CH3:30])=[O:28])=[N:11][N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[C:14](=[O:26])[C:13]=12)C1C=CC=CC=1>CO.[Pd]>[F:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][N:15]2[CH2:16][CH2:17][N:12]3[N:11]=[C:10]([C:27]([O:29][CH3:30])=[O:28])[C:9]([OH:8])=[C:13]3[C:14]2=[O:26])=[CH:24][CH:23]=1

Participants

4

Reactant 1

HCID 68892969Methyl 3-benzyloxy-5-(4-fluorobenzyl)-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate

Product 1

HCID 54722069HCID 54722069, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Nitrogen gas was bubbled through a solution of methyl 3-benzyloxy-5-(4-fluorobenzyl)-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate (37 mg, 0.09 mmol) in MeOH. To the solution was added a small amount of 10% Pd on carbon, and the mixture was stirred under an atmosphere of hydrogen gas overnight. The reaction mixture was filtered through celite, and the filter cake was washed with MeOH. The resulting filtrate was concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, d6-DMSO) δ 9.20 (s, 1H), 7.41-7.37 (m, 2H), 7.21-7.16 (m, 2H), 4.65 (s, 2H), 4.32 (t, J=6.0 Hz, 2H), 3.79 (s, 3H), 3.69 (t, J=6.0H, 2H). HRMS (FT-ICR) C15H14FN3O4+H=320.1047; calculated 320.1041.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe filter cake was washed with MeOH
  3. concentrationThe resulting filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f53a358b75884dc7837c97ac772639e4
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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