HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → 1-Benzhydryl-N-methylazetidine-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-(Diphenylmethyl)azetidine-3-carboxylic acid | HCID 2735440 | — |
| Reactant | Methylamine hydrochloride | HCID 6364545 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 1-Benzhydryl-N-methylazetidine-3-carboxamide | HCID 13772849 | 37.7% |
Reaction Steps
400 mg of 1-benzhydrylazetidin-3-carboxylic acid (synthesized according to the method described in WO2005/49602) was dissolved in 4 ml of dimethylformamide, and 683 mg of triethylamine, 122 mg of methylamine hydrochloride, 304 mg of 1-hydroxybenzotriazole and 431 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were added thereto, and the mixture was stirred at room temperature overnight. The reaction solution was diluted with ethyl acetate. The solution was washed in turn with water and brine and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 158 mg of the objective compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08673891B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-5548a1a452f443ebb26a3f4f707ee79c |
| Source note | uspto-grants-2014_03 |