N-methyl-2-pyrrolidone → 5-Chloro-6-ethyl-3-{[2-methyl-4-(morpholin-4-yl)phenyl]amino}pyrazine-2-carboxamide

HRID 1526216Notes

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:15]1[CH:21]=[C:20]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:19]=[CH:18][C:16]=1[NH2:17].C(N(C(C)C)CC)(C)C.CN1CCCC1=O>O>[Cl:8][C:6]1[N:7]=[C:2]([NH:17][C:16]2[CH:18]=[CH:19][C:20]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:21][C:15]=2[CH3:14])[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 (630 mg), 2-methyl-4-(morpholin-4-yl)aniline (500 mg), diisopropylethylamine (900 μL), and N-methylpyrrolidone (5 mL) was stirred at 110° C. overnight. The reactant was left to be cooled, and then water was added thereto, followed by extraction with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=8:2→5:5) to obtain 5-chloro-6-ethyl-3-{[2-methyl-4-(morpholin-4-yl)phenyl]amino}pyrazine-2-carboxamide (660 mg) as an orange solid.

Workup

waitThe reactant was left
temperatureto be cooled
extractionfollowed by extraction with ethyl acetate
dry with materialThe organic phase was dried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=8:2→5:5)

Sources & evidence

ORD record: ord-952778bd6e584f7cb915f832f2ac41e4
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085540B2

Reaction notes

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