HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetone → (5S)-4-(4,4-Difluorocyclohexyl)-2-[1-(5-{[(2R)-2,3-dihydroxypropyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol dihydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetone | HCID 180 | — |
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | (5S)-4-(4,4-Difluorocyclohexyl)-2-[1-(5-{[(2R)-2,3-dihydroxypropyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol | HCID 71657169 | — |
| Solvent | tert-Butyl methyl ether | HCID 15413 | — |
| Product | (5S)-4-(4,4-Difluorocyclohexyl)-2-[1-(5-{[(2R)-2,3-dihydroxypropyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol dihydrochloride | HCID 71657168 | 50.4% |
Reaction Steps
Reactions similar to those of Example 13 were performed except for using 10.8 μl (130 μmol) of 35% hydrochloric acid and using a mixed solvent of 0.43 ml of acetone and 0.43 ml of tert-butyl methyl ether instead of acetone, and from 43.3 mg (59.9 μmol) of (5S)-4-(4,4-Difluorocyclohexyl)-2-[1-(5-{[(2R)-2,3-dihydroxypropyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol, which was prepared by a method similar to that of Reference Example 27, 24.0 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-cd43089378ce48f09d32f42ed0fbb566 |
| Source note | uspto-grants-2016_04 |