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 66778587 | HCID 66778587 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 66777839 | HCID 66777839 | 56% |
Reaction Steps
A mixture of 6-({1-[5-(cyclopropylmethoxy)-3-methyl-1-benzofuran-2-yl]-2-methylpropyl}amino)pyridine-3-carboxylic acid (145 mg) synthesized above, ethyl 3-(methylamino)propanoate (58 mg), 1-hydroxybenzotriazole.monohydrate (67 mg), triethylamine (122 μL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (84 mg) and N,N-dimethylformamide (2 mL) was stirred at room temperature for 18 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 (104 mg, 56%) 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-5913ee7375e446249c8e89fe5b80df7e |
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| Source note | uspto-grants-2013_05 |
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