Diisopropylethylamine → 5-Chloro-6-ethyl-3-{[3-(methylsulfonyl)phenyl]amino}pyrazine-2-carboxamide
Reaction equation
Cl[C:2]1[C:3]([C:11]([NH2:13])=[O:12])=[N:4][C:5]([CH2:9][CH3:10])=[C:6]([Cl:8])[N:7]=1.[CH3:14][S:15]([C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21])(=[O:17])=[O:16].C(N(CC)C(C)C)(C)C>O1CCOCC1>[Cl:8][C:6]1[N:7]=[C:2]([NH:21][C:20]2[CH:22]=[CH:23][CH:24]=[C:18]([S:15]([CH3:14])(=[O:17])=[O:16])[CH:19]=2)[C:3]([C:11]([NH2:13])=[O:12])=[N:4][C:5]=1[CH2:9][CH3:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 170 °C
Procedure
A mixture of 3,5-dichloro-6-ethylpyrazine-2-carboxamide (600 mg), 3-(methylsulfonyl)aniline (467 mg), N,N-diisopropylethylamine (0.48 mL) and dioxane (18 mL) was stirred in a sealed tube at 170° C. for 17 hours. After cooling, the mixture was partitioned using ethyl acetate and water, and the organic layer was washed with saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was washed with chloroform, and the solid was collected by filtration and dried to give 5-chloro-6-ethyl-3-{[3-(methylsulfonyl)phenyl]amino}pyrazine-2-carboxamide (412 mg) as a yellow solid.
Workup
- temperatureAfter cooling
- customthe mixture was partitioned
- washthe organic layer was washed with saturated aqueous sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- distillationAfter the solvent was distilled off
- washthe residue was washed with chloroform
- filtrationthe solid was collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-27e720ee5f934e30907ce03c2b10d89a
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969336B2
Reaction notes
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