Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Di-tert-butyl (9-bromononyl)imidodicarbonate | HCID 21880675 | — |
| Reactant | (R)-cyclohexyl(phenyl)[1-(piperidin-4-ylmethyl)-1H-1,2,4-triazol-3-yl]methanol | HCID 59145948 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Ammonia | HCID 222 | — |
| Product | Di-tert-butyl{9-[4-({3-[(R)-cyclohexyl(hydroxy)phenylmethyl]-1H-1,2,4-triazol-1-yl}methyl)piperdin-1-yl]nonyl}imidodicarbonate | HCID 59145968 | — |
Reaction Steps
(R)-cyclohexyl(phenyl)[1-(piperidin-4-ylmethyl)-1H-1,2,4-triazol-3-yl]methanol (Preparation 4, 2.00 g, 5.64 mmol) and di-tert-butyl (9-bromononyl)imidodicarbonate (U.S. Pat. No. 4,167,167, 2.38 g, 5.64 mmol) were dissolved in acetonitrile (60 ml) and triethylamine (2.35 ml, 16.9 mmol) added. After stirring at 50° C. for 18 hours, the solvent was removed in vacuo, and the residue purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (98:2:0.2, by volume) to furnish the title compound as a clear oil, in 60% yield, 2.6 g (contains 10% of other triazole regio-isomer)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08263623B2 |
|---|
| Source dataset | uspto-grants-2012_09 |
|---|
| ORD ID | ord-b2d6da3fcc5841689dd3fbf59769be9d |
|---|
| Source note | uspto-grants-2012_09 |
|---|
