Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Chloropyrazine | HCID 73277 | — |
| Reactant | Spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione | HCID 57661820 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 57661836 | HCID 57661836 | 7.4% |
Reaction Steps
A mixture of spiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione (0.150 g, 0.50 mmol), 2-chloropyrazine (0.57 g, 1.67 mmol), triethylamine (0.1 ml, 0.72 mmol), and DMSO (50 ml) was stirred for three hours at 100° C. The crude reaction mixture was purified directly by reverse phase HPLC to give the product as a purple solid (0.014 g, 0.7%) MP=255-256° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.41 (s, 1H), 8.10-8.07 (m, 1H), 7.91-7.81 (m, 3H), 7.76-7.70 (m, 1H), 7.58-7.52 (m, 1H), 4.28-4.22 (m, 2H), 3.39-3.28 (m, 2H), 3.12 (s, 2H), 2.11-2.04 (m, 2H), 1.88-1.79 (m, 2H); LCMS: 380 [M+H].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08039503B2 |
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| Source dataset | uspto-grants-2011_10 |
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| ORD ID | ord-00e4d12c5ec94a3a90c51106536b777c |
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| Source note | uspto-grants-2011_10 |
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