Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | 2,6-Dichloroisonicotinonitrile | HCID 735906 | — |
| Reactant | 2-[(4-fluorophenyl)sulfonyl-ethyl-amino]-N-[[2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]prop-2-enamide | HCID 78319909 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | 2-[(5-chloro-2-thienyl)sulfonyl-ethyl-amino]N-[[2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]prop-2-enamide | HCID 78319913 | — |
| Product | HCID 83074581 | HCID 83074581 | 89% |
Reaction Steps
2,6-dichloropyridine-4-carbonitrile 24 (4 gr, 23.13 mmol) was dissolved in 100 ml of ethanol. To the solution were added TEA (1 equiv., 3.22 ml), morpholine (1 equiv., 2 ml) and the mixture was stirred at 70° C. for 4 hours. (TLC AcOEt 3/petroleum ether 7). The solvent was evaporated and the residue was dissolved with ethyl acetate, washed with water and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The crude was crystallized from ethyl acetate and petroleum ether to give a beige solid. (4.6 g, 89% yield) 1HNMR (DMSO, 400 MHz) δ 3.58 (4H, m), 3.64 (4H, m), 7.10 (1H, s), 7.32 (1H, s)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09409864B2 |
|---|
| Source dataset | uspto-grants-2016_08 |
|---|
| ORD ID | ord-aa930a730be148839c0def30ec789bd8 |
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| Source note | uspto-grants-2016_08 |
|---|
