Methanol → [4-(5-Amino-6-methyl-pyridin-2-yl)-piperazin-1-yl]-(2,6-difluoro-phenyl)-methanone
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[C:19]([CH3:26])[N:18]=2)[CH2:13][CH2:12]1)=[O:10].CO>[Pd].C1COCC1>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([N:14]2[CH2:13][CH2:12][N:11]([C:9]([C:3]3[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[O:10])[CH2:16][CH2:15]2)=[N:18][C:19]=1[CH3:26]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 26 °C
Procedure
Charge (2,6-difluoro-phenyl)-[4-(6-methyl-5-nitro-pyridin-2-yl)-piperazin-1-yl]-methanone (1.00 equiv, 1.44 moles, 520.00 g), methanol (197.66 moles, 8.00 L, 6.33 kg), and THF wetted 5% palladium on carbon (75.00 g) to a three gallon autoclave. Hydrogenate the reaction at 50 psi at room temperature while maintaining a temperature below 30° C. After 0.5 hours, cool to 26° C., and maintain for 2 hours. Filter and concentrate under reduced pressure. Filter to obtain solids, rinse with methanol then heptanes. An additional filtration yields a second batch of [4-(5-amino-6-methyl-pyridin-2-yl)-piperazin-1-yl]-(2,6-difluoro-phenyl)-methanone. Dry under reduced pressure at 45° C. (445 g).
Workup
- customthe reaction at 50 psi at room temperature
- temperaturewhile maintaining a temperature below 30° C
- temperaturemaintain for 2 hours
- filtrationFilter
- concentrationconcentrate under reduced pressure
- filtrationFilter
- customto obtain solids
- washrinse with methanol
- filtrationAn additional filtration
Sources & evidence
- ORD record
- ord-2b1d86aa1887499785dbb62b665be314
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652015B2
Reaction notes
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