Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 58451281 | HCID 58451281 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86657979 | HCID 86657979 | 51% |
Reaction Steps
A solution of N-[5-(5-amino-2-methylphenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (41 mg, 0.12 mmol) produced in Reference Example 1,3-(3-pyridyl)acrylic acid (22 mg, 0.15 mmol), HOBt (20 mg, 0.15 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (28 mg, 0.15 mmmo) in N,N-dimethylformamide (3 mL) was stirred at room temperature overnight. Ethyl acetate (3 mL) and water (3 mL) were added to the reaction mixture, and the organic layer was dehydrated with Presep Tube manufactured by Wako Pure Chemical Industries, Ltd, and concentrated. Dimethyl sulfoxide was added to the residue, and methanol was further added. The precipitate was collected by filtration, washed with methanol and dried to give the title compound (28.6 mg, 51%) as a powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08697874B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-60fa24f810d74266a14199df51e61af3 |
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| Source note | uspto-grants-2014_04 |
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