Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Oxazole | HCID 9255 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 2-Propanol, 2-methyl-, lithium salt (1:1) | HCID 23664764 | — |
| Reactant | 3-[1-(4-Bromophenyl)cyclopropyl]-8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine | HCID 86712858 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86712975 | HCID 86712975 | 106.8% |
Reaction Steps
A solution of the compound (250 mg, 0.49 mmol) obtained in Example 16-4), oxazole (68 mg, 0.98 mmol), tetrakis(triphenylphosphine)palladium(0) (28 mg, 0.02 mmol), and lithium tert-butoxide (81 mg, 0.98 mmol) in dioxane (3 mL) was stirred for 2 h with heating to reflux. The reaction mixture was cooled to room temperature, saturated aqueous ammonium chloride (5 mL) was added to the reaction mixture, the mixture was extracted with ethyl acetate, and the organic layer was washed with saturated sodium chloride solution and dried with anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by silica gel chromatography (ethyl acetate:methanol=70:30) to obtain the title compound (260 mg, quant.) in a yellow oily form.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08927536B2 |
|---|
| Source dataset | uspto-grants-2015_01 |
|---|
| ORD ID | ord-9f7de0f8dbb144398810c03bdcca3894 |
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| Source note | uspto-grants-2015_01 |
|---|
