Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanolamine | HCID 700 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 178472143 | HCID 178472143 | — |
| Reactant | HCID 178479765 | HCID 178479765 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178521296 | HCID 178521296 | 4% |
Reaction Steps
To a solution of N-[(5Z)-5-({1-[2,4-bis(trifluoromethyl)benzyl]piperidin-4-yl}methylidene)-2-oxo-2,5-dihydro-1,3-thiazol-4-yl]glycine hydrochloride (500 mg), N-ethyl-N-(1-methylethyl)propan-2-amine (0.49 mL) and 2-aminoethanol (172 mg) in DMF (5 mL) was added (1-cyano-2-ethoxy-2-oxoethylideneaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate (403 mg), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate), and the solid was recrystallized from diisopropyl ether/heptane to give the title compound (20 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08772277B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-d36d5fe395a14bceb153ec07ff768496 |
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| Source note | uspto-grants-2014_07 |
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