N-methyl-2-pyrrolidone → 6-Ethyl-3-{[2-methyl-4-(morpholin-4-yl)phenyl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide
Reaction equation
Cl[C:2]1[C:3]([C:20]([NH2:22])=[O:21])=[N:4][C:5]([CH2:18][CH3:19])=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[N:7]=1.[CH3:23][C:24]1[CH:30]=[C:29]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[CH:28]=[CH:27][C:25]=1[NH2:26].C(N(C(C)C)CC)(C)C.CN1CCCC1=O>O>[CH2:18]([C:5]1[N:4]=[C:3]([C:20]([NH2:22])=[O:21])[C:2]([NH:26][C:25]2[CH:27]=[CH:28][C:29]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[CH:30][C:24]=2[CH3:23])=[N:7][C:6]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[CH3:19]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 3-chloro-6-ethyl-5-(3-nitrophenoxy)pyrazine-2-carboxamide (300 mg), 2-methyl-4-(morpholin-4-yl)aniline (200 mg), diisopropylethylamine (330 μL), and N-methylpyrrolidone (2 mL) was reacted in a microwave reaction device at 180° C. for 2 hours. The reaction mixture was left to be cooled, and then 5 mL of water was added thereto. The precipitated solid was collected by filtration and purified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:9-7:3) to obtain 6-ethyl-3-{[2-methyl-4-(morpholin-4-yl)phenyl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide (160 mg) as a brown solid.
Workup
- customwas reacted in a microwave reaction device at 180° C. for 2 hours
- waitThe reaction mixture was left
- temperatureto be cooled
- filtrationThe precipitated solid was collected by filtration
- custompurified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:9-7:3)
Sources & evidence
- ORD record
- ord-e712da1d58e144b8b3364888864f4cbc
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09085540B2
Reaction notes
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