Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | Lawesson's reagent | HCID 87949 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 66618765 | HCID 66618765 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66778552 | HCID 66778552 | 10.6% |
Reaction Steps
2-[6-Methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridine-8-carboxylic acid (2-oxo-2-phenylethyl)amide obtained in Example 172 (26.6 mg) was dissolved in THF (1 mL). Lawesson reagent (45.6 mg) was added and the mixture was stirred with heating under reflux for 11 hours. The reaction solution was ice-cooled. Then, chloroform and a saturated sodium bicarbonate solution were added and the organic layer was separated. The resulting organic layer was dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the organic layer was concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography to obtain the title compound (2.8 mg). The compound was further purified by CHIRALCEL™ IB (2 cm×25 cm; mobile phase:hexane:ethanol=30:70) to obtain the title compound (1.5 mg, racemate). The property values of the compound are as follows.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08754100B2 |
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| Source dataset | uspto-grants-2014_06 |
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| ORD ID | ord-d806062fe32144539adc6c2ed4a9c1c1 |
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| Source note | uspto-grants-2014_06 |
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