Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 57901652 | HCID 57901652 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57901625 | HCID 57901625 | 93% |
Reaction Steps
To a mixture of 7-[(2-thienylcarbonyl)amino]-1H-indole-2-carboxylic acid (100 mg), piperidine (42 μL), 1H-1,2,3-benzotriazol-1-ol (75 mg) and N,N-dimethylformamide (4 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (94 mg) at 4° C., and the mixture was stirred at room temperature for 2 days. The reaction mixture was diluted with ethyl acetate, washed with aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:9-6:4) and the obtained oil was recrystallized from diethyl ether to give the title compound (115 mg, yield 93%) as colorless prism crystals. melting point 131-132° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08957070B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-58d49f820e8e4e2092ac703f26fb9e2c |
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| Source note | uspto-grants-2015_02 |
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