Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyrazole | HCID 1048 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | (1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamine | HCID 13822957 | — |
| Reactant | rac-cis-(2-Bromo-5-methylphenyl)(3-methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)methanone | HCID 131737147 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | Trifluoroacetic acid | HCID 6422 | — |
| Product | rac-cis-(3-Methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)(5-methyl-2-(1H-pyrazol-1-yl)phenyl)methanone | HCID 131737158 | — |
Reaction Steps
A mixture of rac-cis-(2-bromo-5-methylphenyl)(3-methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)methanone (0.0326 g, 0.0693 mmol), pyrazole (0.0094 g, 0.139 mmol), (1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine (0.004 g, 0.0277 mmol), Cs2CO3 (0.045 g, 0.139 mmol) and CuI (0.003 g, 0.0139 mmol) and dioxane (1.0 mL) was degassed and heated overnight at 140° C. The reaction was cooled to RT, and acidified with TFA to pH4-5. The solvent was removed in vacuo to obtain the crude which as purified by preparative-HPLC to obtain the title compound as a TFA salt. ESI-MS (m/z): 458, [M+1]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09440982B2 |
|---|
| Source dataset | uspto-grants-2016_09 |
|---|
| ORD ID | ord-d415d17ca0894f4dbc2272ab40ff4ae9 |
|---|
| Source note | uspto-grants-2016_09 |
|---|
