Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Ethoxyethylamine | HCID 66970 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 86641958 | HCID 86641958 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 59331386 | HCID 59331386 | 15% |
Reaction Steps
To a solution of 6-(5-[(1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl]-1H-pyrrol-2-yl)pyridine-3-carboxylic acid (0.170 g) in N,N-dimethylformamide (5 mL) were added 2-ethoxyethylamine (0.056 mL), triethylamine (0.247 mL), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (101 mg) and 1-hydroxybenzotriazole (81 mg), and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=40:60-100:0, volume ratio) and recrystallized from hexane-ethyl acetate to give the title compound (0.029 g, yield 15%) as colorless crystals. MS: 552 (MH+). melting point 87-90° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08318746B2 |
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| Source dataset | uspto-grants-2012_11 |
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| ORD ID | ord-1c56a51fef8b44809bf448d14124f93a |
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| Source note | uspto-grants-2012_11 |
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