Water → Ethyl 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate
Reaction equation
C(O[C:6]1[O:10][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:8][CH:7]=1)CCC.[Cl:16][C:17]1[CH:18]=[C:19]([CH:28]=[CH:29][C:30]=1[F:31])[CH2:20][N:21]1[CH2:26][CH2:25][CH:24]=[CH:23][C:22]1=[O:27].O>>[Cl:16][C:17]1[CH:18]=[C:19]([CH:28]=[CH:29][C:30]=1[F:31])[CH2:20][N:21]1[CH2:26][CH2:25][C:24]2[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:8][CH:7]=[C:6]([OH:10])[C:23]=2[C:22]1=[O:27]Participants
4
Conditions
- Temperature
- 130 °C
Procedure
Ethyl 5-butoxy-1,3-oxazole-2-carboxylate (44.5 g, 208.6 mmol) and 1-(3-chloro-4-fluorobenzyl)-5,6-dihydropyridin-2(1H)-one (25 g, 104.3 mmol) were placed in a heavy walled round bottom flask equipped with a screw top and acid resistant O-ring and a stir bar. The mixture was stirred and water (2.82 mL, 156.7 mmol) was added. The reaction was sealed and placed in an oil bath pre-heated to 130° C. The reaction was aged for 72 hours, when LCMS showed much of the lactam had been consumed. The reaction was allowed to cool and sit until the mass had solidified. The mass was taken up in ether and the solids collected by filtration to give the product as a tan solid. The product was further purified by crystallization from EtOAc.
Workup
- customequipped with a screw top and acid resistant O-ring and a stir bar
- customThe reaction was sealed
- customplaced in an oil bath
- customhad been consumed
- temperatureto cool
- filtrationthe solids collected by filtration
Sources & evidence
- ORD record
- ord-e98c8a2841aa45b885ad890db436cb1d
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07598264B2
Reaction notes
Loading…