Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methane | HCID 297 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Benzoylhydrazine | HCID 11955 | — |
| Reactant | 3-Amino-6-[3-(hydroxymethyl)phenyl]pyrazine-2-carbonitrile | HCID 58710572 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 178508343 | HCID 178508343 | 29% |
Reaction Steps
A mixture of 3-amino-6-[3-(hydroxymethyl)phenyl]pyrazine-2-carbonitrile (0.11 g, 0.5 mmol) and benzoic hydrazide (0.15 g, 1 mmol) were heated at 180-200° C. for 30 min. After cooling, the reaction mass was taken up with 5 mL DMF and the obtained solution was diluted with EtOAc and water, clarified with charcoal and filtered on Celite. The organic layer was separated. After drying over sodium sulfate, the ethyl acetate was evaporated under reduced pressure. Purification of the residue by preparative HPLC (Acetonitrile/water) gave desired product (50 mg): 1H NMR (400 MHz; DMSO-d6): 8.3 (s, 1H); 8.1 (m, 2H); 7.6-7.3 (m, 7H); 5.45 (t, 1H); 4.6 (d, 2H); MS (EI) for C23H22N5OF3 HCl: 442 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07704995B2 |
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| Source dataset | uspto-grants-2010_04 |
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| ORD ID | ord-1d31dba7f196450bbc106bb2d5fa2cc2 |
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| Source note | uspto-grants-2010_04 |
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