Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl diazoacetate | HCID 12192 | — |
| Reactant | HCID 178438590 | HCID 178438590 | — |
| Catalyst | Acetic acid, rhodium(2+) salt | HCID 21674 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 178438679 | HCID 178438679 | 56.6% |
Reaction Steps
A mixture of 4′-{[4-(trans-4-hydroxycyclohexyl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (1.5 g), rhodium(II) acetate (dimer) (0.0070 g) and toluene (15 mL) was heated to 80° C. under an argon atmosphere, a solution of ethyl 2-diazoacetate (1.6 g) in toluene (15 mL) was added dropwise, and the mixture was stirred at 80° C. for 10 min. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (1.0 g, 56%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08921379B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-a2dd8015f84a48f2bffa018b957793cf |
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| Source note | uspto-grants-2014_12 |
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