2-(Methylamino)ethanol → 4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-2-(1-{5-[(2-hydroxyethyl)(methyl)amino]pyrimidin-2-yl}piperidin-4-yl)-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-5,6,7,8-tetrahydroquinoline

HRID 715889Notes

Reaction equation

HRID 715889 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].Br[C:7]1[CH:8]=[N:9][C:10]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]3[C:28]([CH:29]([F:40])[C:30]4[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=4)=[C:27]([CH:41]4[CH2:46][CH2:45][C:44]([F:48])([F:47])[CH2:43][CH2:42]4)[C:26]4[CH:25]([O:49][CH2:50][C:51]5[CH:56]=[CH:55][C:54]([O:57][CH3:58])=[CH:53][CH:52]=5)[CH2:24][C:23]([CH3:60])([CH3:59])[CH2:22][C:21]=4[N:20]=3)[CH2:15][CH2:14]2)=[N:11][CH:12]=1>>[F:48][C:44]1([F:47])[CH2:43][CH2:42][CH:41]([C:27]2[C:26]3[CH:25]([O:49][CH2:50][C:51]4[CH:52]=[CH:53][C:54]([O:57][CH3:58])=[CH:55][CH:56]=4)[CH2:24][C:23]([CH3:59])([CH3:60])[CH2:22][C:21]=3[N:20]=[C:19]([CH:16]3[CH2:17][CH2:18][N:13]([C:10]4[N:11]=[CH:12][C:7]([N:2]([CH2:3][CH2:4][OH:5])[CH3:1])=[CH:8][N:9]=4)[CH2:14][CH2:15]3)[C:28]=2[CH:29]([F:40])[C:30]2[CH:35]=[CH:34][C:33]([C:36]([F:37])([F:39])[F:38])=[CH:32][CH:31]=2)[CH2:46][CH2:45]1

Participants

3

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 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 866824694-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-2-(1-{5-[(2-hydroxyethyl)(methyl)amino]pyrimidin-2-yl}piperidin-4-yl)-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-5,6,7,8-tetrahydroquinolineYield 26%

Procedure

Reactions similar to those of Reference Example 13 were performed except for using 2-(methylamino)ethanol instead of isonipecotic acid ethyl ester, and from 100 mg (0.120 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, 25 mg of 4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-2-(1-{5-[(2-hydroxyethyl)(methyl)amino]pyrimidin-2-yl}piperidin-4-yl)-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-5,6,7,8-tetrahydroquinoline was obtained (yield: 26%).

Sources & evidence

ORD record
ord-9e2e5e9bf4a14b1b8575629fffc3a087
Source dataset
uspto-grants-2015_11
Patent number
US09187450B2

Reaction notes

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