HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethylmorpholine → N-((tetrahydro-2H-pyran-4-yl)methyl)-2-((1-(4-(trifluoromethyl)benzyl)-3-((((4-(trifluoromethyl)benzyl)oxy)imino)methyl)-1H-indol-5-yl)oxy)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 | (Oxan-4-yl)methanamine hydrochloride | HCID 44118690 | — |
| Reactant | HCID 76528216 | HCID 76528216 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-((tetrahydro-2H-pyran-4-yl)methyl)-2-((1-(4-(trifluoromethyl)benzyl)-3-((((4-(trifluoromethyl)benzyl)oxy)imino)methyl)-1H-indol-5-yl)oxy)acetamide | HCID 76528446 | 68% |
Reaction Steps
To a solution of compound prepared in example 8 (250 mg, 0.454 mmoles) in DMF (2 mL), (tetrahydro-2H-pyran-4-yl)methanamine hydrochloride (83 mg, 0.545 mmoles), HOBT (Catalyst), EDC.HCl (130 mg, 0.681 mmoles) and N-ethyl morpholine (0.173 ml, 1.362 mmoles) were added and the reaction mixture was srirred at 25° C. for 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 purified by column chromatography to yield 200 mg (68%) 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-75460e64c3064df2b069acc18a7b9421 |
| Source note | uspto-grants-2014_09 |