Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 22710404 | HCID 22710404 | — |
| Reactant | HCID 22711147 | HCID 22711147 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 22710697 | HCID 22710697 | 65.2% |
Reaction Steps
In N,N-dimethylformamide (1 ml), 1-[(6-chloronaphthalen-2-yl)sulfonyl]-6-methoxycarbonyl-1,2,3,4-tetrahydropyrazine (60 mg) and p-nitrophenyl 4-(pyridin-4-yl)benzoate (52 mg) were dissolved, followed by the addition of sodium hydride (60% in oil, 7.20 mg) under ice cooling. The resulting mixture was stirred for 1 hour. Water and ethyl acetate were added to the reaction mixture to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate and the solvent was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (ethyl acetate:hexane=2:1), followed by dissolution in ethanol. To the resulting solution, 1N aqueous hydrochloric acid in ethanol was added and the resulting mixture was concentrated, whereby the title compound (58 mg, 60%) was obtained as pale yellow powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06747023B1 |
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| Source dataset | uspto-grants-2004_06 |
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| ORD ID | ord-5b88af2d63504edf852cd1e633778e32 |
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| Source note | uspto-grants-2004_06 |
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