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

HRID 715872Notes

Reaction equation

HRID 715872 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[CH:4][N:3]=1.BrC1C=NC(Cl)=NC=1.[F:23][C:24]1([F:70])[CH2:29][CH2:28][CH:27]([C:30]2[C:39]3[CH:38]([O:40]CC4C=CC(OC)=CC=4)[CH2:37][C:36]([CH3:51])([CH3:50])[CH2:35][C:34]=3[N:33]=[C:32]([CH:52]3[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]3)[C:31]=2[CH:58]([F:69])[C:59]2[CH:64]=[CH:63][C:62]([C:65]([F:68])([F:67])[F:66])=[CH:61][CH:60]=2)[CH2:26][CH2:25]1>>[F:70][C:24]1([F:23])[CH2:29][CH2:28][CH:27]([C:30]2[C:39]3[CH:38]([OH:40])[CH2:37][C:36]([CH3:50])([CH3:51])[CH2:35][C:34]=3[N:33]=[C:32]([CH:52]3[CH2:57][CH2:56][N:55]([C:2]4[N:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[CH:4][N:3]=4)[CH2:54][CH2:53]3)[C:31]=2[CH:58]([F:69])[C:59]2[CH:64]=[CH:63][C:62]([C:65]([F:67])([F:68])[F:66])=[CH:61][CH:60]=2)[CH2:26][CH2:25]1

Participants

4

Reactant 3

HCID 6066655-Bromo-2-chloropyrimidineHCID 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 86682446Pyrimidine, 2-chloro-5-(4,4,4-trifluorobutyl)-

Product 1

HCID 866824454-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-2-{1-[5-(4,4,4-trifluorobutyl)pyrimidin-2-yl]piperidin-4-yl}-5,6,7,8-tetrahydroquinolin-5-ol

Procedure

Reactions similar to those of the first step of Example 2 and Example 38 were performed except for using 2-chloro-5-(4,4,4-trifluorobutyl) pyrimidine, which was prepared by a method similar to that of Reference Example 26, instead of 5-bromo-2-chloropyrimidine, and from 70 mg (0.10 mmol) 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, 45 mg of the title compound was obtained as a white solid (yield: 61%).

Workup

  1. customwas prepared by a method similar to that of Reference Example 26

Sources & evidence

ORD record
ord-6fc5e388bbf1446cba79594fa989bf8b
Source dataset
uspto-grants-2015_11
Patent number
US09187450B2

Reaction notes

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