Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 2-(2-(O-tolylamino)benzo[d]oxazol-6-yl)acetic acid | HCID 23508315 | — |
| Reactant | 4-(2-Methylamino-ethoxy)-benzoic acid methyl ester | HCID 23512029 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Catalyst | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 17858822 | HCID 17858822 | 80% |
Reaction Steps
In DMF (6 ml) were dissolved 2-(2-methylphenylamino)-6-benzoxazolylacetic acid (154 mg, 0.55 mmol) and methyl 4-(2-(N-methylamino)ethoxy)benzoate (117 mg, 0.55 mmol). To the resulting solution were added EDC HCl (157 mg, 0.81 mmol), HOBt (5 mg, 0.04 mmol), and DMAP (5 mg, 0.04 mmol). The resulting mixture was stirred at room temperature for 18 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from chloroform-methanol (10:1, v/v) eluate fractions, methyl 4-(2-((2-(2-methylphenylamino)-6-benzoxazolyl)-N-methylacetamido)ethoxy)benzoate (207 mg, 80%) was obtained as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07157487B2 |
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| Source dataset | uspto-grants-2007_01 |
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| ORD ID | ord-45c2b8892105472a9791d30cbcf97cd0 |
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| Source note | uspto-grants-2007_01 |
|---|
