HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethylmorpholine → 2,2'-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)oxazol-2-yl)azanediyl)bis(N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide)
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethylmorpholine | HCID 7525 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 4-Aminomethyltetrahydropyran | HCID 2773210 | — |
| Reactant | 2,2'-((5-(1-(((4-(Trifluoromethyl)benzyl)oxy)imino)ethyl)oxazol-2-yl)azanediyl)diacetic acid | HCID 76528215 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2,2'-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)oxazol-2-yl)azanediyl)bis(N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide) | HCID 76528445 | 49.2% |
Reaction Steps
To a solution of compound prepared in example 6 (250 mg, 0.60 mmoles) in DMF (2 mL), (tetrahydro-2H-pyran-4-yl)methanamine (138 mg, 1.20 mmoles), HOBT (121 mg, 0.90 mmoles), EDC.HCl (138 mg, 0.72 mmoles) and N-ethyl morpholine (227 μL, 1.80 mmoles) were added and reaction mixture was srirred at 25° C. for 2-5 hours under nitrogen atmosphere. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The combined ethyl acetate extract was washed with water & brine, dried over sodium sulphate and evaporated under reduced pressure. The crude product was triturated with hexane to yield 180 mg (49%) of product as white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08822414B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-c689f77a9752451b98bc9ba6fd90e553 |
| Source note | uspto-grants-2014_09 |