Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Reactant | 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline | HCID 2734655 | — |
| Reactant | HCID 88569548 | HCID 88569548 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 117667470 | HCID 117667470 | 55.8% |
Reaction Steps
Under an argon atmosphere, to a mixture of 5-chloro-6-ethyl-3-({3-methyl-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (200 mg), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (93 mg), and N-methylpyrrolidone (2 mL) were added tetrakistriphenylphosphine palladium (0) (25 mg) and a 2 M aqueous sodium carbonate solution (424 μL), followed by stirring in a microwave reaction device at 100° C. for 1 hour. Water was added thereto, and the solid was collected by filtration. The obtained solid was purified by silica gel column chromatography (eluent: chloroform:methanol:28% aqueous ammonia=1:0:0-100:10:1) to obtain 5-(3-aminophenyl)-6-ethyl-3-({3-methyl-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (125 mg) as an orange solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09085540B2 |
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| Source dataset | uspto-grants-2015_07 |
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| ORD ID | ord-5ac53f5e087145888ef513500492720d |
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| Source note | uspto-grants-2015_07 |
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