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 86657980 | HCID 86657980 | 11% |
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-phenylprop-2-ynoic acid (21 mg, 0.15 mmol), HOBt (20 mg, 0.15 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (28 mg, 0.15 mmol) 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. The residue was dissolved in dimethyl sulfoxide, and purified by preparative HPLC. The obtained fraction was concentrated to give the title compound (6.3 mg, 11%) 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-8ce9a19534af433bb594512fc6913018 |
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| Source note | uspto-grants-2014_04 |
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