HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → N-Benzyloxy-N-{1-[N'-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclohexylmethyl}-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}cyclohexane-1-carboxylic acid | HCID 58016118 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-Benzyloxy-N-{1-[N'-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclohexylmethyl}-formamide | HCID 86606473 | 47% |
Reaction Steps
To a mixture of 1-[(Benzyloxy-formyl-amino)-methyl]-cyclohexanecarboxylic acid (0.10 g, 0.34 mmol), 2-hydrazino-4-(trifluoromethyl)pyrimidine (0.06 g, 0.34 mmol), NMM (0.17 g, 1.7 mmol) and HOAt (0.046 g, 0.34 mmol) in DMF (2 mL) at room temperature was added 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide hydrochloride (0.067 g, 0.34 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 (0.070 g, 47%). MH+452.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07332485B2 |
| Source dataset | uspto-grants-2008_02 |
| ORD ID | ord-e66942a60497444482ae36b5f35ddf44 |
| Source note | uspto-grants-2008_02 |