HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanesulfonic Acid → (5S)-4-(4,4-Difluorocyclohexyl)-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-2-(1-{5-[3-hydroxy-2-(hydroxymethyl)-2-methylpropoxy]pyrimidin-2-yl}piperidin-4-yl)-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol methanesulfonate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanesulfonic Acid | HCID 6395 | — |
| Reactant | (5S)-4-(4,4-Difluorocyclohexyl)-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-2-(1-{5-[3-hydroxy-2-(hydroxymethyl)-2-methylpropoxy]pyrimidin-2-yl}piperidin-4-yl)-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol | HCID 71656789 | — |
| Solvent | tert-Butyl methyl ether | HCID 15413 | — |
| Product | (5S)-4-(4,4-Difluorocyclohexyl)-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-2-(1-{5-[3-hydroxy-2-(hydroxymethyl)-2-methylpropoxy]pyrimidin-2-yl}piperidin-4-yl)-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol methanesulfonate | HCID 117687920 | 50.7% |
Reaction Steps
Reactions similar to those of Example 3 were performed except for using 4.5 μl (0.069 mmol) of methanesulfonic acid instead of 47% hydrobromic acid salt and using 2.5 ml of tert-butyl methyl ether instead of methyl ethyl ketone, and from 51.8 mg (0.069 mmol) of (5S)-4-(4,4-Difluorocyclohexyl)-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-2-(1-{5-[3-hydroxy-2-(hydroxymethyl)-2-methylpropoxy]pyrimidin-2-yl}piperidin-4-yl)-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol, which was prepared by a method similar to that of Reference Example 19, 29 mg of the title compound was obtained as a white powder (yield: 50%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09321747B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-73d68ebc811749c9af9a771e5a74684c |
| Source note | uspto-grants-2016_04 |