Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Methanesulfonamide | HCID 72879 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 50902001 | HCID 50902001 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 60151297 | HCID 60151297 | 72.1% |
Reaction Steps
Under an argon atmosphere, to a solution of 6-(6-methyl-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxylic acid (838 mg) in dichloromethane (17.4 mL) were added methane sulfonamide (279 mg), 4-dimethylaminopyridine (718 mg), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.13 g) successively, and this mixture was stirred at room temperature for 24 hours. To the reaction mixture was added 1 mol/L hydrochloric acid, followed by extraction with dichloromethane. The organic layer was washed with 1 mol/L hydrochloric acid, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: methanol-dichloromethane) to obtain the title compound (740 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08815903B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-a3d8aef060744d7daeb5fc47ad6ebf30 |
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| Source note | uspto-grants-2014_08 |
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