Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Pentanone | HCID 7895 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | p-Toluenesulfonic acid monohydrate | HCID 521998 | — |
| Reactant | 3-Amino-5-(pyridin-4-yl)thiophene-2-carboxamide | HCID 9920852 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Product | HCID 66744251 | HCID 66744251 | 44% |
Reaction Steps
A mixture of 3-amino-5-(pyridin-4-yl)thiophene-2-carboxamide (0.108 g, 0.500 mmol), 2-pentanone (3.0 mL), p-toluenesulfonic acid monohydrate (0.0095 g, 0.050 mmol) and acetic acid (3.0 mL) was stirred for 2 h at 70° C. then for 3 h at 80° C. in a sealed tube. The mixture was poured into sat. aqueous sodium hydrogen carbonate (150 mL). Extraction with ethyl acetate-tetrahydrofuran (2:1, 150 mL), drying over magnesium sulfate, filtration and concentration at reduced pressure gave an oil. The oil was triturated with dichloromethane, and the precipitate was collected by filtration to afford the title compound (0.0632 g, 44%) 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-bc69ba54adbf4f318686a6a4b8723bc2 |
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| Source note | uspto-grants-2014_04 |
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