1-Iodo-3-methylbutane → (-)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-2-{1-[5-(3-methylbutoxy)pyrimidine-2-yl]piperidin-4-yl}-5,6,7,8-tetrahydroquinoline-5-ol

HRID 715862Notes

Reaction equation

HRID 715862 reaction equation
I[CH2:2][CH2:3][CH:4]([CH3:6])[CH3:5].[F:7][C:8]1([F:52])[CH2:13][CH2:12][CH:11]([C:14]2[C:23]3[CH:22]([OH:24])[CH2:21][C:20]([CH3:26])([CH3:25])[CH2:19][C:18]=3[N:17]=[C:16]([CH:27]3[CH2:32][CH2:31][N:30]([C:33]4[N:38]=[CH:37][C:36]([OH:39])=[CH:35][N:34]=4)[CH2:29][CH2:28]3)[C:15]=2[CH:40]([F:51])[C:41]2[CH:46]=[CH:45][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:43][CH:42]=2)[CH2:10][CH2:9]1>>[F:52][C:8]1([F:7])[CH2:9][CH2:10][CH:11]([C:14]2[C:23]3[CH:22]([OH:24])[CH2:21][C:20]([CH3:25])([CH3:26])[CH2:19][C:18]=3[N:17]=[C:16]([CH:27]3[CH2:28][CH2:29][N:30]([C:33]4[N:38]=[CH:37][C:36]([O:39][CH2:2][CH2:3][CH:4]([CH3:6])[CH3:5])=[CH:35][N:34]=4)[CH2:31][CH2:32]3)[C:15]=2[CH:40]([F:51])[C:41]2[CH:42]=[CH:43][C:44]([C:47]([F:49])([F:48])[F:50])=[CH:45][CH:46]=2)[CH2:12][CH2:13]1

Participants

3

Reactant 2

HCID 109241-Iodo-3-methylbutaneHCID 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 76372466(-)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-2-{1-[5-(3-methylbutoxy)pyrimidine-2-yl]piperidin-4-yl}-5,6,7,8-tetrahydroquinoline-5-ol

Procedure

Reactions similar to those of Example 21 were performed except for using 62 (0.47 mmol) of 1-iodo-3-methylbutane instead of 1-iodo-2-methylpropane, and from 55 mg (0.085 mmol) 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, 40 mg of the title compound was obtained as a white solid (yield: 65%).

Sources & evidence

ORD record
ord-682ce4ae6ca042dc9bdd8cea9e6a63fb
Source dataset
uspto-grants-2015_11
Patent number
US09187450B2

Reaction notes

Loading…