Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 5-Chloro-2-fluorobenzoic acid | HCID 2736537 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | 5-Tert-butyl-3-butyl-1,3,4-thiadiazol-2(3h)-imine | HCID 66643349 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | HCID 178448747 | HCID 178448747 | — |
Reaction Steps
To a mixture of Example 162C (250 mg, 1.17 mmol), 1H-benzo[d][1,2,3]triazol-1-ol hydrate (179 mg, 1.17 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (225 mg, 1.17 mmol), 5-chloro-2-fluorobenzoic acid (205 mg, 1.17 mmol) in 8 mL of THF was added triethylamine (163 μL, 1.17 mmol). The mixture was heated at 70° C. for 12 hours then cooled to ambient temperature and diluted with ethyl acetate and aqueous NaHCO3. The organic extract was concentrated and the residue was purified by chromatography on SiO2 using an Analogix® Intelliflash280™ (Hex-EtOAc, 0 to 30% gradient) to give the title compound. LC/MS m/z 369 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08859596B2 |
|---|
| Source dataset | uspto-grants-2014_10 |
|---|
| ORD ID | ord-c487aa13339245ae9e16ccaaa608ebc4 |
|---|
| Source note | uspto-grants-2014_10 |
|---|
