Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanolamine | HCID 700 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 57736404 | HCID 57736404 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 57736417 | HCID 57736417 | — |
Reaction Steps
To a solution of 5-[(2,5-difluorophenyl)[(4-ethoxyphenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxylic acid (112 mg, 0.25 mmol) in methylene chloride (3 ml), 2-aminoethanol (0.017 ml, 0.28 mmol), 1-hydroxybenzotriazole (37 mg, 0.28 mmol), 4-methylmorpholine (0.030 ml, 0.28 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (53 mg, 0.28 mmol) were added at room temperature. After stirring for 3 hours at room temperature, the reaction mixture was washed with water and then saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the obtained residue was subjected to flash silica gel chromatography. The fraction obtained from an elution with hexane:ethyl acetate=1:2 was concentrated under reduced pressure, and the resulting residue was washed with a mixed solvent of ethanol and diethyl ether, and was collected by filtration to obtain the title compound mg, 0.20 mmol, 79%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08114886B2 |
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| Source dataset | uspto-grants-2012_02 |
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| ORD ID | ord-4479bb1b6c2649a2a31e4c8e2d9558e1 |
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| Source note | uspto-grants-2012_02 |
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