HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl 3-(4-{6-[N'-(4-methoxybenzoyl)-hydrazinocarbonyl]-1H-indol-2-yl}-3,5-dimethyl-phenyl)-propionate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 4-Methoxybenzohydrazide | HCID 76792 | — |
| Reactant | 2-[4-(2-Methoxycarbonylethyl)-2,6-dimethylphenyl]-1H-indole-6-carboxylic acid | HCID 66966205 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 3-(4-{6-[N'-(4-methoxybenzoyl)-hydrazinocarbonyl]-1H-indol-2-yl}-3,5-dimethyl-phenyl)-propionate | HCID 66966407 | — |
Reaction Steps
To a mixture of 2-[4-(2-methoxycarbonylethyl)-2,6-dimethylphenyl]-1H-indole-6-carboxylic acid (200 mg, 570 μmol) and HOBT (85 mg, 630 μmol) in THF (10 mL) was added EDCI (164 mg, 860 μmol) and the solution was stirred at RT for 10 min. Then a solution of 4-methoxybenzoic acid hydrazide (104 mg, 630 μmols) in THF (5 mL) was added and the mixture was stirred at RT for 18 h. The solvent was removed under reduced pressure and the residual material was chromatographed using a 50-90% gradient of heptane/ethyl acetate to give the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08217065B2 |
| Source dataset | uspto-grants-2012_07 |
| ORD ID | ord-72d2f6701efc4ffd9cdcdc110f3b8d3f |
| Source note | uspto-grants-2012_07 |