Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Propylamine | HCID 7852 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | HCID 59484992 | HCID 59484992 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 59485013 | HCID 59485013 | 36.4% |
Reaction Steps
A solution of DMF (1.0 mL) containing {5-[4-(4-methoxyphenyl)piperazin-1-yl]-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl}acetic acid (50 mg, 0.118 mmol) synthesized in Example 141, propylamine (45 mg, 0.236 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (45 mg, 0.236 mmol), 1-hydroxybenzotriazol monohydrate (36 mg, 0.236 mmol) and triethylamine (60 mg, 0.590 mmol) was stirred at room temperature for 15 hours, and the reaction solution was distributed using water and ethyl acetate. The organic layer was washed with saturated saline and dried using anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane-ethyl acetate 90:10-70:30) and crystallized from ethyl acetate-hexane to obtain 20 mg of the title compound (yield 36%). Melting point was 135 to 138° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08957069B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-102b045e0e104d9f8ddf1eb194db7bac |
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| Source note | uspto-grants-2015_02 |
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