HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → N-Benzyloxy-N-{1-[N'-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclopentylmethyl}-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}cyclopentane-1-carboxylic acid | HCID 71416985 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-Benzyloxy-N-{1-[N'-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclopentylmethyl}-formamide | HCID 86606471 | 57% |
Reaction Steps
To a mixture of 1-[(Benzyloxy-formyl-amino)-methyl]-cyclopentanecarboxylic acid (0.10 g, 0.36 mmol), 2-hydrazino-4-(trifluoromethyl)pyrimidine (0.10 g, 0.43 mmol), NMM (0.11 g, 1.08 mmol) and HOAt (0.059 g, 0.43 mmol) in DMF (2 mL) at room temperature was added 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide hydrochloride (0.085 g, 0.43 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 (0.085 g, 57%). MH+438.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07332485B2 |
| Source dataset | uspto-grants-2008_02 |
| ORD ID | ord-e450fe8d6bae461b9194caa733f08bc7 |
| Source note | uspto-grants-2008_02 |