HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyanoacetic acid → HCID 24693565, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyanoacetic acid | HCID 9740 | — |
| Reactant | 3-(Trifluoromethyl)benzylamine | HCID 75962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 24693565 | HCID 24693565 | 51% |
Reaction Steps
Cyanoacetic acid (297.0 mg, 3.5 mmol), N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide hydrochloride (1.34 g, 7.0 mmol), 1-hydroxybenzotriazole hydrate (641.0 mg, 4.2 mmol) and DIPEA (1.8 g, 14.0 mmol) and 3-(trifluoromethyl)benzylamine (611.0 mg, 3.5 mmol) were suspended in THF. The mixture was heated to 60° for 18 h. Water was added to the mixture and the product extracted with EtOAc, dried over MgSO4 and concentrated. The crude product was purified by flash chromatography, CH2Cl2/MeOH 98:2, yielding 430.0 mg (51%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08415333B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-bd5c82ef080a44eea61236908d39738d |
| Source note | uspto-grants-2013_04 |