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

HRID 715856Notes

Reaction equation

HRID 715856 reaction equation
[CH:1](I)([CH3:3])[CH3:2].[F:5][C:6]1([F:50])[CH2:11][CH2:10][CH:9]([C:12]2[C:21]3[CH:20]([OH:22])[CH2:19][C:18]([CH3:24])([CH3:23])[CH2:17][C:16]=3[N:15]=[C:14]([CH:25]3[CH2:30][CH2:29][N:28]([C:31]4[N:36]=[CH:35][C:34]([OH:37])=[CH:33][N:32]=4)[CH2:27][CH2:26]3)[C:13]=2[CH:38]([F:49])[C:39]2[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:41][CH:40]=2)[CH2:8][CH2:7]1>>[F:50][C:6]1([F:5])[CH2:7][CH2:8][CH:9]([C:12]2[C:21]3[CH:20]([OH:22])[CH2:19][C:18]([CH3:23])([CH3:24])[CH2:17][C:16]=3[N:15]=[C:14]([CH:25]3[CH2:26][CH2:27][N:28]([C:31]4[N:36]=[CH:35][C:34]([O:37][CH:1]([CH3:3])[CH3:2])=[CH:33][N:32]=4)[CH2:29][CH2:30]3)[C:13]=2[CH:38]([F:49])[C:39]2[CH:40]=[CH:41][C:42]([C:45]([F:47])([F:46])[F:48])=[CH:43][CH:44]=2)[CH2:10][CH2:11]1

Participants

3

Reactant 2

HCID 6362Isopropyl iodideHCID 76372263(-)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-2-[1-(5-hydroxypyrimidin-2-yl)piperidin-4-yl]-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol

Product 1

HCID 76372363(-)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-2-{1-[5-(propan-2-yloxy)pyrimidin-2-yl]piperidin-4-yl}-5,6,7,8-tetrahydroquinolin-5-ol

Procedure

Reactions similar to those of Example 13 were performed except for using isopropyl iodide instead of ethyl iodide and setting the reaction temperature to 50° C., and from 60 mg (90 μmol) of (−)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-2-[1-(5-hydroxypyrimidin-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 Example 4, 54 mg of the title compound was obtained as a white solid (yield: 90%).

Workup

  1. customto 50° C.

Sources & evidence

ORD record
ord-2688e1297bce4aa0b4111f2866d93529
Source dataset
uspto-grants-2015_11
Patent number
US09187450B2

Reaction notes

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