Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetone | HCID 180 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | p-Toluenesulfonic acid monohydrate | HCID 521998 | — |
| Reactant | HCID 66743627 | HCID 66743627 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Product | HCID 66743881 | HCID 66743881 | 62% |
Reaction Steps
A mixture of 3-(propylamino)-5-(pyridin-4-yl)thiophene-2-carboxamide (0.130 g, 0.500 mmol), acetone (3.0 mL), p-toluenesulfonic acid monohydrate (0.0095 g, 0.050 mmol) and acetic acid (2.0 mL) was stirred for 2 days at 70° C. in a sealed tube. The mixture was poured into sat. aqueous sodium hydrogen carbonate (100 mL). Extraction with ethyl acetate-tetrahydrofuran (2:1, 100 mL), drying over magnesium sulfate, filtration and concentration at reduced pressure gave an oil. The oil was purified by column chromatography (Combiflash, 12 g silica gel, hexane to ethyl acetate), then washed with ethyl acetate to afford the title compound (0.094 g, 62%) as a yellow solid:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08691828B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-be9337bf1404426891390ad8027cd94e |
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| Source note | uspto-grants-2014_04 |
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