Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 89580918 | HCID 89580918 | — |
| Reactant | HCID 178425242 | HCID 178425242 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178425162 | HCID 178425162 | 94.1% |
Reaction Steps
To a solution of 4-(1-(3-bromophenoxy)ethyl)benzoic acid (0.9 g, 2.8 mmol), 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.77 g, 4.0 mmol) and 1-hydroxybenzotriazole (0.54 g, 4.0 mmol) in dichloromethane (20 mL) was added triethylamine (0.8 g, 8.0 mmol). The reaction mixture was stirred for 15 minutes at room temperature, then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (0.76 g, 5 mmol) was added. The reaction mixture was stirred at room temperature for 12 hours. After the reaction, the mixture was washed with water (20 mL), concentrated and purified by column chromatography (silica gel: dichloromethane: methanol=20:1) to give pure product 4-(1-(3-bromophenoxy)ethyl)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide (1.2 g, 93%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09206128B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-eb24bd92cdc7466789bbc18a6d379b0d |
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| Source note | uspto-grants-2015_12 |
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