HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → 2-[4-Bromo-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | methyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate hydrochloride | HCID 45074056 | — |
| Reactant | 4-Bromo-3-(2-m-tolyl-ethoxy)-benzoic acid | HCID 67076639 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-[4-Bromo-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid methyl ester | HCID 67076435 | 90.3% |
Reaction Steps
The compound of step 2 (0.410 g, 1.22 mmol) was dissolved in DMF (5 ml), EDIA (0.790 g, 6.12 mmol), HOBT (33 mg, 0.244 mmol), and 2-amino-indane-2-carboxylic acid methyl ester hydrochloride (0.246 g, 1.47 mmol) were added, the mixture was cooled in an ice bath and EDC (352 mg, 1.84 mmol) was added. The mixture was stirred overnight. The volatiles were evaporated in vacuo, the mixture was partitioned between 2 N hydrochloric acid and EA, the organic phase was dried over magnesium sulfate and evaporated to dryness. The residue was purified by silica gel chromatography (HEP/EA gradient) to give 0.56 g of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08802720B2 |
| Source dataset | uspto-grants-2014_08 |
| ORD ID | ord-8557e58237224ad8b8b3ee7c7cce5b9f |
| Source note | uspto-grants-2014_08 |