Glyoxal → 1-Benzyl-3-(naphthalen-2-yl)-1H-pyrazolo[3,4-b]pyrazine

HRID 34068

Reaction equation

HRID 34068 reaction equation
[CH2:1]([N:8]1[C:12]([NH2:13])=[C:11]([NH2:14])[C:10]([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:25]([CH:27]=O)=O>CO>[CH2:1]([N:8]1[C:12]2=[N:13][CH:25]=[CH:27][N:14]=[C:11]2[C:10]([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7860GlyoxalHCID 230701962-benzyl-5-(naphthalen-2-yl)-2H-pyrazole-3,4-diamine

Product 1

HCID 597972851-Benzyl-3-(naphthalen-2-yl)-1H-pyrazolo[3,4-b]pyrazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

190 mg of 2-benzyl-5-(naphthalen-2-yl)-2H-pyrazole-3,4-diamine was dissolved in 10 mL of methanol, added with 100 μl of 40% glyoxal aqueous solution, and stirred at room temperature for 5 hours. The reaction solution was partitioned between water and ethyl acetate, and the organic layer was extracted and washed with water. The organic layer was dried over magnesium sulfate, the solvent was evaporated, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5), to afford 180 mg of the title compound as a pale yellow powder.

Workup

  1. customThe reaction solution was partitioned between water and ethyl acetate
  2. extractionthe organic layer was extracted
  3. washwashed with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-2a5fe7c910be4257badd2215126efe90
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Linked notes

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