1,4-Dioxane → 5-chloro-3-({4-[(2S)-2,4-dimethylpiperazin-1-yl]phenyl}amino)-6-ethylpyrazine-2-carboxamide

HRID 1526187Notes

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][C@H:15]1[CH2:20][N:19]([CH3:21])[CH2:18][CH2:17][N:16]1[C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1.C(N(C(C)C)CC)(C)C.O1CCOCC1>O>[Cl:8][C:6]1[N:7]=[C:2]([NH:26][C:25]2[CH:24]=[CH:23][C:22]([N:16]3[CH2:17][CH2:18][N:19]([CH3:21])[CH2:20][C@@H:15]3[CH3:14])=[CH:28][CH:27]=2)[C:3]([C:11]([NH2:13])=[O:12])=[N:4][C:5]=1[CH2:9][CH3:10]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 3,5-dichloro-6-ethylpyrazine-2-carboxamide (420 mg), 4-[(2S)-2,4-dimethylpiperazin-1-yl]aniline (392 mg), diisopropylethylamine (665 μL), and dioxane (8.4 mL) was stirred at 110° C. overnight. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=95:5) to obtain 5-chloro-3-({4-[(2S)-2,4-dimethylpiperazin-1-yl]phenyl}amino)-6-ethylpyrazine-2-carboxamide (560 mg) as a brown solid.

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic phase was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=95:5)

Sources & evidence

ORD record: ord-d27d009c947c4d899d3e662268493b82
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085540B2

Reaction notes

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