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

HRID 715882Notes

Reaction equation

HRID 715882 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[CH:4][N:3]=1.ClC1N=CC(OC2CCN(C)CC2)=CN=1.[F:30][C:31]1([F:77])[CH2:36][CH2:35][CH:34]([C:37]2[C:46]3[CH:45]([O:47]CC4C=CC(OC)=CC=4)[CH2:44][C:43]([CH3:58])([CH3:57])[CH2:42][C:41]=3[N:40]=[C:39]([CH:59]3[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]3)[C:38]=2[CH:65]([F:76])[C:66]2[CH:71]=[CH:70][C:69]([C:72]([F:75])([F:74])[F:73])=[CH:68][CH:67]=2)[CH2:33][CH2:32]1>>[F:77][C:31]1([F:30])[CH2:36][CH2:35][CH:34]([C:37]2[C:46]3[CH:45]([OH:47])[CH2:44][C:43]([CH3:57])([CH3:58])[CH2:42][C:41]=3[N:40]=[C:39]([CH:59]3[CH2:64][CH2:63][N:62]([C:2]4[N:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[CH:4][N:3]=4)[CH2:61][CH2:60]3)[C:38]=2[CH:65]([F:76])[C:66]2[CH:71]=[CH:70][C:69]([C:72]([F:74])([F:75])[F:73])=[CH:68][CH:67]=2)[CH2:33][CH2:32]1

Participants

4

Reactant 3

HCID 86682426(-)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-2-(piperidin-4-yl)-5,6,7,8-tetrahydroquinolineHCID 866824592-Chloro-5-[(1-methylpiperidin-4-yl)oxy]pyrimidineHCID 866824642-Chloro-5-(3,3,3-trifluoropropoxy)pyrimidine

Product 1

HCID 86682463(-)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-2-{1-[5-(3,3,3-trifluoropropoxy)pyrimidin-2-yl]piperidin-4-yl}-5,6,7,8-tetrahydroquinolin-5-ol

Procedure

Reactions similar to those of Reference Example 29 and Example 38 were performed except for using 2-chloro-5-(3,3,3-trifluoropropoxy) pyrimidine, which was prepared by a method similar to that of Reference Example 31, instead of 2-chloro-5-[(1-methylpiperidin-4-yl)oxy]pyrimidine, and from 150 mg (222 μmol) of (−)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-2-(piperidin-4-yl)-5,6,7,8-tetrahydroquinoline, which was prepared by a method similar to that of Reference Example 10, 85 mg of the title compound was obtained as a white solid (yield: 51%).

Workup

  1. customwas prepared by a method similar to that of Reference Example 31

Sources & evidence

ORD record
ord-c5618714ed594e5c9002e48378af3f21
Source dataset
uspto-grants-2015_11
Patent number
US09187450B2

Reaction notes

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