HuagongsheHuagongshe Chemistry Print Report · For research reference only
1H-Indole-3-ethanamine, 5-methoxy-, hydrochloride (1:?) → 2-(4-Cyano-3-trifluoromethyl-phenoxy)-4-methyl-pentanoic acid [2-(5-methoxy-1H-indol-3-yl)-ethyl]-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1H-Indole-3-ethanamine, 5-methoxy-, hydrochloride (1:?) | HCID 6198 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | HCID 18366554 | HCID 18366554 | — |
| Reactant | HCID 57598540 | HCID 57598540 | — |
| Reactant | 1-(Dimethylaminopropyl)-3-ethylcarbodiimide 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride | HCID 86630846 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-(4-Cyano-3-trifluoromethyl-phenoxy)-4-methyl-pentanoic acid [2-(5-methoxy-1H-indol-3-yl)-ethyl]-amide | HCID 57598470 | — |
Reaction Steps
The compound was prepared in the following manner. To 0.25 gm (0.83 mmol) of 2-(4-cyano-3-trifluoromethyl-phenoxy)-4-methyl-pentanoic acid in dimethylformamdie “DMF” (15 mL) were added 0.14 gm (1.04 mmol) of 1-Hydroxy-benzotriazole HOBT, 0.2 gm (1.04 mmol) of (3-(dimethylamino)propyl)ethylcarbodiimide EDCl, 0.23 gm (2.28 mmol) N-methyl morpholine, and approximately 234 mg of 5-methoxytryptamine hydrochloride (1.04 mmol). The resultant mixtures were stirred at room temperature for approximately 18 hours. The reactions were quenched with sodium bicarbonate (20 mL) and extracted with ethyl acetate (3 times 20 mL). The solvent was removed in vacuo to obtain oils that were then purified by HPLC.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07507860B2 |
| Source dataset | uspto-grants-2009_03 |
| ORD ID | ord-3169ad53d41a41a3a8c9ea8043dc34d8 |
| Source note | uspto-grants-2009_03 |