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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 632596Generated: October 29, 2026

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 dihydrobromide

https://huagongshe.com/reaction/632596

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetoneHCID 180—
ReactantHydrogen BromideHCID 260—
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-olHCID 71657169—
Solventtert-Butyl methyl etherHCID 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 dihydrobromideHCID 7165717060.4%

Reaction Steps

Reactions similar to those of Example 13 were performed except for using 17.3 μl (152 μmol) of 47% hydrobromic acid instead of 35% hydrochloric acid and using 0.50 ml of a 1:1 mixed solvent of acetone and tert-butyl methyl ether instead of acetone, and from 49.5 mg (68.5 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, 36.6 mg of the title compound was obtained as a white powder (yield: 60%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09321747B2
Source datasetuspto-grants-2016_04
ORD IDord-18b12ce9cf774158967eee97e2670813
Source noteuspto-grants-2016_04