HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Tert-butyl 4-{6-[5-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenylaminocarbonyl)-2-methyl-phenoxy]-pyrimidin-4-carbonyl}-piperazine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-3-hydroxy-4-methyl-benzamide | HCID 67217566 | — |
| Reactant | Tert-butyl 4-(6-chloro-pyrimidin-4-carbonyl)-piperazine-1-carboxylate | HCID 86664519 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Tert-butyl 4-{6-[5-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenylaminocarbonyl)-2-methyl-phenoxy]-pyrimidin-4-carbonyl}-piperazine-1-carboxylate | HCID 67491403 | — |
Reaction Steps
75 mg potassium-tert-butoxide are added at ambient temperature under an argon atmosphere to 225 mg N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-3-hydroxy-4-methyl-benzamide in 3 ml N,N-dimethylformamide. After ten minutes 210 mg tert-butyl 4-(6-chloro-pyrimidin-4-carbonyl)-piperazine-1-carboxylate are added, and the reaction mixture is stirred for six days at ambient temperature. For working up the reaction mixture is mixed with water and extracted with ethyl acetate. The combined ethyl acetate extracts are washed with saturated sodium chloride solution, dried on magnesium sulphate and evaporated down. The flask residue is chromatographed through a silica gel column with cyclohexane/ethyl acetate (50:50→20:80).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08946438B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-202284c67431468496db52e94c93a551 |
| Source note | uspto-grants-2015_02 |