1,2-Dimethoxyethane → (-)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-2-{1-[5-(4-hydroxypiperidin-1-yl)pyrimidin-2-yl]piperidin-4-yl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol

HRID 715853Notes

Reaction equation

HRID 715853 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.COCCOC.Br[C:15]1[CH:16]=[N:17][C:18]([N:21]2[CH2:26][CH2:25][CH:24]([C:27]3[C:36]([CH:37]([F:48])[C:38]4[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=4)=[C:35]([CH:49]4[CH2:54][CH2:53][C:52]([F:56])([F:55])[CH2:51][CH2:50]4)[C:34]4[CH:33]([O:57]CC5C=CC(OC)=CC=5)[CH2:32][C:31]([CH3:68])([CH3:67])[CH2:30][C:29]=4[N:28]=3)[CH2:23][CH2:22]2)=[N:19][CH:20]=1>C1(C)C=CC=CC=1>[F:56][C:52]1([F:55])[CH2:51][CH2:50][CH:49]([C:35]2[C:34]3[CH:33]([OH:57])[CH2:32][C:31]([CH3:67])([CH3:68])[CH2:30][C:29]=3[N:28]=[C:27]([CH:24]3[CH2:23][CH2:22][N:21]([C:18]4[N:19]=[CH:20][C:15]([N:5]5[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]5)=[CH:16][N:17]=4)[CH2:26][CH2:25]3)[C:36]=2[CH:37]([F:48])[C:38]2[CH:39]=[CH:40][C:41]([C:44]([F:45])([F:47])[F:46])=[CH:42][CH:43]=2)[CH2:54][CH2:53]1

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 79341Piperidin-4-olHCID 866824252-[1-(5-Bromopyrimidin-2-yl)piperidin-4-yl]-4-(4,4-difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-5,6,7,8-tetrahydroquinoline

Product 1

HCID 76372315(-)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-2-{1-[5-(4-hydroxypiperidin-1-yl)pyrimidin-2-yl]piperidin-4-yl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Reactions similar to those of Reference Example 13 and Example 7 were performed except for using 4-hydroxy piperidine and 1,2-dimethoxyethane instead of isonipecotic acid ethyl ester and toluene, and from 150 mg (0.180 mmol) of (−)-2-[1-(5-Bromopyrimidin-2-yl)piperidin-4-yl]-4-(4,4-difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-5,6,7,8-tetrahydroquinoline, which was prepared by a method similar to that of Reference Example 11, 55 mg of the title compound was obtained as a light yellow solid (yield: 42%).

Sources & evidence

ORD record
ord-4250992e2cb14627b1b7bdcecacbc7b5
Source dataset
uspto-grants-2015_11
Patent number
US09187450B2

Reaction notes

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