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

HRID 632581Notes

Reaction equation

HRID 632581 reaction equation
[BrH:1].[F:2][C:3]1([F:53])[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][CH:36]([CH2:39][OH:40])[CH2:37][OH:38])=[CH:30][N:29]=4)[CH2:24][CH2:23]3)[C:10]=2[C@@H:41]([F:52])[C:42]2[CH:47]=[CH:46][C:45]([C:48]([F:51])([F:50])[F:49])=[CH:44][CH:43]=2)[CH2:5][CH2:4]1>>[BrH:1].[BrH:1].[F:53][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]([CH3:20])([CH3:21])[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][CH:36]([CH2:39][OH:40])[CH2:37][OH:38])=[CH:30][N:29]=4)[CH2:24][CH2:23]3)[C:10]=2[C@@H:41]([F:52])[C:42]2[CH:47]=[CH:46][C:45]([C:48]([F:49])([F:51])[F:50])=[CH:44][CH:43]=2)[CH2:7][CH2:8]1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 71656703(5S)-4-(4,4-Difluorocyclohexyl)-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-2-(1-{5-[3-hydroxy-2-(hydroxymethyl)propoxy]pyrimidin-2-yl}piperidin-4-yl)-7,7-dimethyl-5,6,7,8-tetrahydr oquinolin-5-ol

Product 1

HCID 71656787(5S)-4-(4,4-Difluorocyclohexyl)-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-2-(1-{5-[3-hydroxy-2-(hydroxymethyl)propoxy]pyrimidin-2-yl}piperidin-4-yl)-7,7-dimethyl-5,6,7,8-tetrahydr oquinolin-5-ol dihydrobromide

Procedure

Reactions similar to those of Example 1 were performed except for using 0.22 ml of 47% hydrobromic acid instead of 35% hydrochloric acid, and from 0.70 g (0.95 mmol) of (5S)-4-(4,4-Difluorocyclohexyl)-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-2-(1-{5-[3-hydroxy-2-(hydroxymethyl)propoxy]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 22, 741 mg of the title compound was obtained as a white powder (yield: 88%).

Sources & evidence

ORD record
ord-60ea0cb18dfd494b96e0d10984d565e7
Source dataset
uspto-grants-2016_04
Patent number
US09321747B2

Reaction notes

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