HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetone → (5S)-4-(4,4-Difluorocyclohexyl)-2-[1-(5-{[(2S)-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 dihydrobromide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetone | HCID 180 | — |
| Reactant | Hydrogen Bromide | HCID 260 | — |
| Reactant | HCID 71657166 | HCID 71657166 | — |
| Solvent | tert-Butyl methyl ether | HCID 15413 | — |
| Product | (5S)-4-(4,4-Difluorocyclohexyl)-2-[1-(5-{[(2S)-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 dihydrobromide | HCID 71657167 | 75.3% |
Reaction Steps
Reactions similar to those of Example 13 were performed except for using 13.0 μl (114 μmol) of 47% hydrobromic acid instead of 35% hydrochloric acid and using 0.37 ml of a 1:1 mixed solvent of acetone and tert-butyl methyl ether instead of acetone, and from 37.0 mg (51.2 μmol) of (5S)-4-(4,4-Difluorocyclohexyl)-2-[1-(5-{[(2S)-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 25, 34.1 mg of the title compound was obtained as a white powder (yield: 75%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09321747B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-eb5d12897a11495a98b6c159221bf220 |
| Source note | uspto-grants-2016_04 |