Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 3-Fluoropyridine-4-carboxylic acid | HCID 345361 | — |
| Reactant | HCID 58148233 | HCID 58148233 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 66879858 | HCID 66879858 | 62.7% |
Reaction Steps
A mixture of 1.5 g of 6-amino-1,1,3,3-tetrafluoro-5-hydroxy-1,3-dihydroisobenzofuran, 0.95 g of 3-fluoroisonicotinic acid, 1.68 g of WSC and 13 ml of pyridine was stirred while heating at 80° C. for two hours. The reaction mixture was cooled to room temperature, and then water was added, followed by extraction with ethyl acetate three times. The combined organic layers were washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.46 g of 3-fluoro-N-(1,1,3,3-tetrafluoro-6-hydroxy-1,3-dihydroisobenzofuran-5-yl)isonicotinamide.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08324387B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-f0f3a9ab9bf2473d8dde6e987791988f |
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| Source note | uspto-grants-2012_12 |
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