HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → 1-Methyl-N-(tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]-1H-imidazole-4-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1-methyl-1H-imidazole-4-carboxylic acid | HCID 541509 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | N-[3-(Trifluoromethoxy)benzyl]tetrahydro-2H-pyran-4-amine | HCID 58049381 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 1-Methyl-N-(tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]-1H-imidazole-4-carboxamide | HCID 46916684 | 14.4% |
Reaction Steps
A mixture of N-[3-(trifluoromethoxy)benzyl]tetrahydro-2H-pyran-4-amine (450 mg), 1-methyl-1H-imidazole-4-carboxylic acid (210 mg), EDC.HCl (320 mg), HOBt (250 mg) and acetonitrile (5 mL) was stirred at room temperature for an hour. Acetonitrile was distilled off under reduced pressure and an aqueous solution of 6 M sodium hydroxide was added. Extraction was conducted with ethyl acetate and the solvent was concentrated. The residue was purified by column chromatography (NH silica gel cartridge; ethyl acetate) to give the titled compound (90 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08623898B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-3e3ee17d43a4428ba849d0dfde4e66d7 |
| Source note | uspto-grants-2014_01 |