Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Ethyl 3-(methylamino)propanoate | HCID 541480 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 66777998 | HCID 66777998 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 66777824 | HCID 66777824 | 73% |
Reaction Steps
A mixture of 5-({1-[5-(cyclopropylmethoxy)-3-methyl-1-benzofuran-2-yl]-2-methylpropyl}amino)pyridine-2-carboxylic acid (311 mg) synthesized above, ethyl 3-(methylamino)propanoate (131 mg), 1-hydroxybenzotriazole.monohydrate (145 mg), triethylamine (265 μL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (182 mg) and N,N-dimethylformamide (2 mL) was stirred at room temperature for 16 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate 100:0-0:100, v/v) to give the title compound (291 mg, 73%) as a colorless amorphous form.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08436043B2 |
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| Source dataset | uspto-grants-2013_05 |
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| ORD ID | ord-d9e9c134c385424bb09d7c244c70d713 |
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| Source note | uspto-grants-2013_05 |
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