Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | HCID 66872362 | HCID 66872362 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66872348 | HCID 66872348 | 74% |
Reaction Steps
The compound (50 mg) obtained in Example 56 was dissolved in DMF (1.0 mL), then N,N-diisopropylethylamine (0.030 mL), ammonium chloride (8 mg), 1-hydroxybenzotriazole hydrate (22 mg) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (27 mg) were added thereto in that order, and stirred at room temperature for 3 days. Water was added to the reaction liquid, and extracted four times with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried with sodium sulfate. The drying agent was removed through filtration, and the solvent was evaporated off under reduced pressure. The residue was purified through silica gel column chromatography (methanol/chloroform=from 0% to 20%, gradient) to give the entitled compound (37 mg, 74%) as a colorless solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08420823B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-10d5bc9a688044098f97046ca7d2d0a8 |
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| Source note | uspto-grants-2013_04 |
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