HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → N-Benzyloxy-N-{3-butyl-1-[N'-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclobutylmethyl}-formamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | HOAt | HCID 181649 | — |
| Reactant | 2-Hydrazino-4-(trifluoromethyl)pyrimidine | HCID 1268079 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | (1-[(Benzyloxy-formyl-amino)-methyl)]-3-butyl-cyclobutanecarboxylic acid | HCID 86606490 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-Benzyloxy-N-{3-butyl-1-[N'-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclobutylmethyl}-formamide | HCID 86606489 | 47.1% |
Reaction Steps
To a mixture of (1-[(benzyloxy-formyl-amino)-methyl)]-3-butyl-cyclobutanecarboxylic acid (0.10 g, 0.31 mmol), 2-hydrazino-4-(trifluoromethyl)pyrimidine (0.067 g, 0.37 mmol), NMM (0.095 g, 0.93 mmol) and HOAt (0.05 g, 0.37 mmol) in DMF (3 mL) at room temperature was added 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide hydrochloride (0.072 g, 0.37 mmol). After stirring at room temperature 18 h, the reaction mixture was then purified by preparative, reverse-phase HPLC to afford the title compound as a white solid (0.07 g, 47%). MH+480.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07332485B2 |
| Source dataset | uspto-grants-2008_02 |
| ORD ID | ord-c60bae1143114005886c70c12e880249 |
| Source note | uspto-grants-2008_02 |