Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cyclopropanemethanamine | HCID 75646 | — |
| Reactant | Trimethylaluminum | HCID 16682925 | — |
| Reactant | HCID 25130783 | HCID 25130783 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 25131099 | HCID 25131099 | 78% |
Reaction Steps
A solution of trimethylaluminium (2 M in toluene, 338 μL, 0.68 mmol) and cyclopropanemethylamine (60.4 μL, 0.68 mmol) in dioxane (9 mL) was stirred at room temperature for 1 h and then a solution of 4-[4-(3-phenyl-5-trifluoromethyl-isoxazol-4-yl)-imidazol-1-yl]-benzoic acid methyl ester (70 mg, 0.17 mmol) in dioxane (6 mL) was added. The resulting mixture was then heated at 85-95° C. overnight and then cooled to room temperature and then poured into water and extracted with ethyl acetate which was then washed with brine, dried over sodium sulphate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=60:40) afforded the title compound (60 mg, 78%) which was obtained as a colourless oil. MS: m/e=453.3 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07851469B2 |
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| Source dataset | uspto-grants-2010_12 |
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| ORD ID | ord-2446760d8edd43b59cb75934d820eb8f |
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| Source note | uspto-grants-2010_12 |
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