HuagongsheHuagongshe Chemistry Print Report · For research reference only
Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 6-chloro-N3-[5-(dimethylphosphoryl)-3-methoxypyrazin-2-yl]-N5-[2-(propan-2-ylsulfonyl)phenyl]-1,2,4-triazine-3,5-diamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- | HCID 18462 | — |
| Reactant | 5-(Dimethylphosphoryl)-3-methoxypyrazin-2-amine | HCID 67052682 | — |
| Reactant | 3,6-dichloro-N-[2-(propan-2-ylsulfonyl)phenyl]-1,2,4-triazin-5-amine | HCID 86668822 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 6-chloro-N3-[5-(dimethylphosphoryl)-3-methoxypyrazin-2-yl]-N5-[2-(propan-2-ylsulfonyl)phenyl]-1,2,4-triazine-3,5-diamine | HCID 86668827 | — |
Reaction Steps
A mixture of 3,6-dichloro-N-[2-(propan-2-ylsulfonyl)phenyl]-1,2,4-triazin-5-amine (prepared as in Example 106: 0.7 mmol), 5-(dimethylphosphoryl)-3-methoxypyrazin-2-amine (0.7 mmol) and camphorsulfonic acid (0.7 equiv.), is refluxed for 20-48 hours in 2-propanol. The reaction mixture is allowed to cool to room temperature, dissolved in dichloromethane and washed with an aqueous solution of Na2CO3. The dichloromethane extract is dried over MgSO4 and evaporated. The crude product is purified by Prep-HPLC.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09012462B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-299a3d990ee14291870cc9af75760532 |
| Source note | uspto-grants-2015_04 |