Hydrogen Bromide → (5S)-4-(4,4-Difluorocyclohexyl)-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-2-(1-{5-[3-(methylsulfonyl)propoxy]pyrimidin-2-yl}piperidin-4-yl)-5,6,7,8-tetrahydroquinolin-5-ol dihydrobromide

HRID 632598Notes

Reaction equation

HRID 632598 reaction equation
[BrH:1].[F:2][C:3]1([F:54])[CH2:8][CH2:7][CH:6]([C:9]2[C:18]3[C@@H:17]([OH:19])[CH2:16][C:15]([CH3:21])([CH3:20])[CH2:14][C:13]=3[N:12]=[C:11]([CH:22]3[CH2:27][CH2:26][N:25]([C:28]4[N:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][S:38]([CH3:41])(=[O:40])=[O:39])=[CH:30][N:29]=4)[CH2:24][CH2:23]3)[C:10]=2[C@@H:42]([F:53])[C:43]2[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:45][CH:44]=2)[CH2:5][CH2:4]1>CC(C)=O>[BrH:1].[BrH:1].[F:54][C:3]1([F:2])[CH2:4][CH2:5][CH:6]([C:9]2[C:18]3[C@@H:17]([OH:19])[CH2:16][C:15]([CH3:21])([CH3:20])[CH2:14][C:13]=3[N:12]=[C:11]([CH:22]3[CH2:27][CH2:26][N:25]([C:28]4[N:29]=[CH:30][C:31]([O:34][CH2:35][CH2:36][CH2:37][S:38]([CH3:41])(=[O:39])=[O:40])=[CH:32][N:33]=4)[CH2:24][CH2:23]3)[C:10]=2[C@@H:42]([F:53])[C:43]2[CH:44]=[CH:45][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:47][CH:48]=2)[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 71604910HCID 71604910, compound

Product 1

HCID 71657273(5S)-4-(4,4-Difluorocyclohexyl)-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-2-(1-{5-[3-(methylsulfonyl)propoxy]pyrimidin-2-yl}piperidin-4-yl)-5,6,7,8-tetrahydroquinolin-5-ol dihydrobromideYield 56.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Reactions similar to those of Example 13 were performed except for using 13.2 μl (116 μmol) of 47% hydrobromic acid instead of 35% hydrochloric acid and using 0.40 ml of acetone, and from 40.0 mg (52.0 μmol) of (5S)-4-(4,4-Difluorocyclohexyl)-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-2-(1-{5-[3-(methylsulfonyl)propoxy]pyrimidin-2-yl}piperidin-4-yl)-5,6,7,8-tetrahydroquinolin-5-ol, which was prepared by a method similar to that of Reference Example 28, 27.2 mg of the title compound was obtained as a white powder (yield: 56%).

Sources & evidence

ORD record
ord-4ae5f084511e469a8834e8ebd396d10b
Source dataset
uspto-grants-2016_04
Patent number
US09321747B2

Reaction notes

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