Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 2-Bromoethylamine hydrobromide | HCID 2774217 | — |
| Reactant | N-[2-Amino-4-(5-methyl-[1,2,4]oxadiazol-3-yl)-benzyl]-3,5-dimethoxy-4-methyl-benzamide | HCID 69491883 | — |
| Catalyst | Tetrabutylammonium Iodide | HCID 67553 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 69491452 | HCID 69491452 | 49.4% |
Reaction Steps
To a solution of compound 1g (114 mg, 0.3 mmol) and pyridine (0.049 mL, 0.60 mmol) in DMF was added 2-bromoethylamine hydrobromide (92 mg, 0.45 mmol). The reaction mixture was heated at 80° C. for three days. After two days, additional 2-bromoethylamine hydrobromide (100 mg) and tetrabutylammonium iodide (5 mg) was added. The reaction was diluted with water and made basic by addition of 1 N NaOH. The solid was recovered by filtration and washed with water. The solid was purified by preparative thin layer chromatography (9:1 chloroform/methanol) to give compound 44a (63 mg, 49%). ESI-MS m/e 426.3 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07247654B2 |
|---|
| Source dataset | uspto-grants-2007_07 |
|---|
| ORD ID | ord-4ca86f5d45d14f2692398926a9a64a40 |
|---|
| Source note | uspto-grants-2007_07 |
|---|
