p-Toluenesulfonic acid monohydrate → 3-{4-Chloro-2-fluoro-5-[(propoxycarbonyl)methoxy]phenyl}-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine

HRID 849948Notes

Reaction equation

HRID 849948 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][C:5]([C:14]2[C:15](=[O:25])[N:16]([CH3:24])[C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][N:19]=2)=[C:4]([F:26])[CH:3]=1.O.[C:28]1(C)C=CC(S(O)(=O)=O)=C[CH:29]=1>C(O)CC>[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]([O:12][CH2:13][CH2:28][CH3:29])=[O:11])=[CH:6][C:5]([C:14]2[C:15](=[O:25])[N:16]([CH3:24])[C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][N:19]=2)=[C:4]([F:26])[CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 193654823-{4-Chloro-2-fluoro-5-[(methoxycarbonyl)methoxy]phenyl}-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine2×

Product 1

HCID 193655083-{4-Chloro-2-fluoro-5-[(propoxycarbonyl)methoxy]phenyl}-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazineYield 342%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

To a solution of 100 mg of 3-{4-chloro-2-fluoro-5-[(methoxycarbonyl)methoxy]phenyl}-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-165) in 1.0 ml of propanol was added 10 mg of p-toluenesulfonic acid monohydrate, and the mixture was heated under reflux for 5 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and the excess propanol was distilled out under reduced pressure. The residue was subjected to silica gel column chromatography, which afforded 76 mg (yield, 71%) of 3-{4-chloro-2-fluoro-5-[(propoxycarbonyl)methoxy]phenyl}-1-methyl-6-trifluoromethyl-2-oxo -1,2-dihydropyrazine (present compound 1-167).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customAfter completion of the reaction
  4. distillationthe excess propanol was distilled out under reduced pressure

Sources & evidence

ORD record
ord-95d60403f6ab4d72896ac14b5c481e51
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

Loading…