Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Cyclopropanecarboxylic acid | HCID 15655 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | HCID 131729246 | HCID 131729246 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ammonium Chloride | HCID 25517 | — |
| Product | HCID 67212307 | HCID 67212307 | — |
Reaction Steps
[5-(2-Ethylaminomethyl-4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic acid methyl ester, dihydrochloride (0.108 g, 0.25 mmol), cyclopropanecarboxylic acid (0.02 mL, 0.30 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.073 g, 0.38 mmol), 1-hydroxybenzotriazole hydrate (0.051 g, 0.38 mmol), and triethylamine (0.16 mL, 1.14 mmol) were combined in CH2Cl2 (1 mL) and stirred at room temperature for 45 minutes. The mixture was diluted with aqueous NH4Cl and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give (5-{2-[(N-cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid methyl ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08049015B2 |
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| Source dataset | uspto-grants-2011_11 |
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| ORD ID | ord-e645b36b959843b6b3e95ba36a4f5d49 |
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| Source note | uspto-grants-2011_11 |
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