HCID 70557130, compound → HCID 70558596, compound
Reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[C:13]([O:15]C)=[O:14]>CO.O>[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH:2]1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[C:13]([OH:15])=[O:14]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a solution of methyl 4-(2-pyrazinyl)-3-pyridinecarboxylate (400 mg; may be prepared as described in Intermediate 19) in methanol (20 mL) and water (3 mL) LiOH was added (44.5 mg). The reaction mixture was stirred at 80° C. for 2 h. The reaction mixture was filtered to remove the inorganic salts and evaporated in vacuo. The residue was dissolved in MeOH (20 ml), Pd/C (300 mg) was added and the reaction mixture was placed under hydrogen at 3 bar for 2 days. The reaction was monitored by LCMS which showed complete conversion of starting material. Then the catalyst was filtered by means of a celite plug and the filter was washed with MeOH. Then the solvent was evaporated in vacuo and the residue dissolved in 25 ml of MeOH to give a solution of the title compound, used directly in subsequent reactions.
Workup
- filtrationThe reaction mixture was filtered
- customto remove the inorganic salts
- customevaporated in vacuo
- dissolutionThe residue was dissolved in MeOH (20 ml)
- additionPd/C (300 mg) was added
- waitthe reaction mixture was placed under hydrogen at 3 bar for 2 days
- filtrationThen the catalyst was filtered by means of a celite plug
- washthe filter was washed with MeOH
- customThen the solvent was evaporated in vacuo
- dissolutionthe residue dissolved in 25 ml of MeOH
Sources & evidence
- ORD record
- ord-f5ca118362fe427ea962af5d3c47b64a
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933132B2
Reaction notes
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