HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Chloroquinoxaline → (1R,6S)-8-(6-Methyl-2-trifluoromethyl-pyrimidin-4-yl)-3,8-diaza-bicyclo[4.2.0]octane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Chloroquinoxaline | HCID 238938 | — |
| Reactant | 4-Chloro-6-methyl-2-(trifluoromethyl)pyrimidine | HCID 25067267 | — |
| Reactant | Tert-butyl 3,8-diazabicyclo[4.2.0]octane-3-carboxylate | HCID 43810891 | — |
| Reactant | 2-(3,8-Diaza-bicyclo[4.2.0]oct-8-yl)-quinoxaline | HCID 67116651 | — |
| Product | (1R,6S)-8-(6-Methyl-2-trifluoromethyl-pyrimidin-4-yl)-3,8-diaza-bicyclo[4.2.0]octane | HCID 68156957 | — |
Reaction Steps
The title compound was prepared in a manner analogous to Intermediate 2, substituting (1R,6S)-(3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester for 3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester and 4-chloro-2-trifluoromethyl-6-methyl-pyrimidine for 2-chloro-quinoxaline in Step A. MS (ESI) mass calcd. for C12H15F3N4, 272.27; m/z found 273.0 [M+H]+. 1H NMR (CDCl3): 6.29 (s, br, 1H), 6.13 (s, 1H), 4.52 (d, J=8.0, 1H), 4.08-3.94 (m, 1H), 3.87-3.75 (m, 1H), 3.64 (t, J=19.8, 1H), 3.39-3.26 (m, 1H), 3.11 (dd, J=14.2, 3.5, 1H), 3.00-2.77 (m, 2H), 2.38 (s, 3H), 2.22-2.07 (m, 1H), 1.92-1.79 (m, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08680275B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-5c458a5266eb41559d59d9c9e4f6a021 |
| Source note | uspto-grants-2014_03 |