Ammonia → 6-[1-(4-chlorophenyl)-1H-pyrazol-5-yl]-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[N:18]=[C:17]([C:19]([O:21]C)=O)[C:16](=[O:23])[N:15]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=4)[C:14]=3[CH3:34])=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:3]=1.CO.[NH3:37]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[N:18]=[C:17]([C:19]([NH2:37])=[O:21])[C:16](=[O:23])[N:15]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:32])([F:31])[F:33])[CH:25]=4)[C:14]=3[CH3:34])=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:3]=1Participants
4
Reactant 3
Product 1
Conditions
- Temperature
- 60 °C
Procedure
Methyl 6-[1-(4-chlorophenyl)-pyrazol-5-yl]-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylate (0.0915 g, 0.187 mmol) was dissolved in 7M ammonia in methanol (4.0 mL, 28 mmol) and heated in a microwave reactor (Biotage) at 60° C. for 7 minutes. The violet coloured solution was concentrated by rotary evaporation. The crude product was purified by semi-preparative reversed phase-HPLC (Kromasil C18 column) with acetonitrile-water (60 to 97% MeCN) as eluent to give 6-[1-(4-chlorophenyl)-1H-pyrazol-5-yl]-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide (0.0636 g, 72%) as a light yellow solid.
Workup
- concentrationwas concentrated by rotary evaporation
- customThe crude product was purified by semi-preparative reversed phase-HPLC (Kromasil C18 column) with acetonitrile-water (60 to 97% MeCN) as eluent
Sources & evidence
- ORD record
- ord-e90b4ccc145e42cc9aef86033dc145bc
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466284B2
Reaction notes
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