Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methylamine | HCID 6329 | — |
| Reactant | 1H-Indole-5-Carboxylic Acid | HCID 74280 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 22103818 | HCID 22103818 | 73.5% |
Reaction Steps
In 5 mL of N,N-dimethylformamide, 500 mg (3.1 mmol) of 1H-indole-5-carboxylic acid, 750 mg (9.3 mmol) of 40% methylamine, 477 mg (3.1 mmol) of benzotriazole-1-ol hydrate and 713 mg (3.8 mmol) of (3-dimethylaminopropyl)ethylcarbodiimide hydrochloride were dissolved and the solution was stirred at room temperature for three hours, and then the solvent was distilled under reduced pressure. The obtained residue was dissolved in ethyl acetate and washed with a saturated sodium hydrogencarbonate solution (50 mL, twice) and a saturated saline (50 mL) in the order named. The organic layer was dried and then concentrated to obtain 397 mg (73%) of a crude product of 1H-indole-5-carboxylic acid methylamide. The product was used in the next reaction without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08609656B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-41bbcb1f6c254e8b8e240920527996fb |
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| Source note | uspto-grants-2013_12 |
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