Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Phenyl chloroformate | HCID 15891 | — |
| Reactant | 4-Bromo-2,6-diaminopyridine | HCID 11435393 | — |
| Reactant | HCID 67273585 | HCID 67273585 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 42630483 | HCID 42630483 | 14.1% |
Reaction Steps
The below prepared benzofuran-3-sulfonic acid amide (0.051 g, 0.259 mmol) was dissolved in 1.5 mL of abs. acetonitrile and treated successively with triethylamine (0.090 mL, 2.5 eq.) and phenyl chloroformate (0.0405 g, 1.0 eq.), and the mixture was then kept at ambient temperature for 1 h. 4-Bromo-pyridine-2,6-diamine (0.0486 g, 1.0 eq.), dissolved in a tiny amount of acetonitrile, was added, and the mixture heated to 60° C. for 18 h. Cooling, pouring onto crashed ice, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=3/7) and crystallization from AcOEt/heptane, yielded finally 0.015 g of the title compound as off-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08163778B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-2ab788bbff504d09a7bd4ac1d2ad2398 |
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| Source note | uspto-grants-2012_04 |
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