Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Methylamine | HCID 6329 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | HCID 22259324 | HCID 22259324 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 22259355 | HCID 22259355 | 93% |
Reaction Steps
1,1′-Carbonyldiimidazole (143 mg) was added to a solution of 2-[1-[4-[4-[[2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methoxy]phenyl]butyl]-1H-imidazol-2-yl]-1-ethanol (300 mg) in THF (3 ml) at 0° C., and the mixture was stirred at the same temperature for 3 hr. A solution (2.0 M; 1.47 ml) of methylamine in THF was added to the reaction mixture at 0° C., and the mixture was stirred at the same temperature for 3 hr and at room temperature for 30 min. The reaction mixture was combined with water and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure and recrystallized from diethyl ether-acetone-hexane to give the titled compound (310 mg) as a colorless crystal powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06984653B2 |
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| Source dataset | uspto-grants-2006_01 |
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| ORD ID | ord-a896d211b6f14926b452755110e110c1 |
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| Source note | uspto-grants-2006_01 |
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