HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → ethyl 4-[3-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl-N-methylamino]-1-propyl]benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 3-Methoxy-4-o-tolylureidophenylacetic acid | HCID 11449840 | — |
| Reactant | Ethyl 4-(3-methylamino-1-propyl)benzoate | HCID 23512152 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | ethyl 4-[3-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl-N-methylamino]-1-propyl]benzoate | HCID 23512235 | 71% |
Reaction Steps
To a stirred solution of 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetic acid (456 mg, 1.45 mmol) and ethyl 4-(3-methylamino-1-propyl)benzoate (220 mg, 1.45 mmol) were added EDC.HCl (417 mg, 2.16 mmol), HOBt (cat.), and DMAP (catalytic amount) in DMF (10 mL), and the resulting mixture was stirred overnight. The mixture was diluted with EtOAc (300 mL), washed with brine, dried over MgSO4, and evaporated. The residue was chromatographed on silica-gel with CHCl3—EtOH (10:1) to give 503 mg (71%) ethyl 4-[3-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl-N-methylamino]-1-propyl]benzoate as a yellow oil. MS (FAB) m/z 518(M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06756378B2 |
| Source dataset | uspto-grants-2004_06 |
| ORD ID | ord-10e5d9c3e0864646a7497e397bfc2344 |
| Source note | uspto-grants-2004_06 |