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

HRID 715854Notes

Reaction equation

HRID 715854 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:4][N:3]=1.[F:11][C:12]1([F:58])[CH2:17][CH2:16][CH:15]([C:18]2[C:27]3[CH:26]([O:28]CC4C=CC(OC)=CC=4)[CH2:25][C:24]([CH3:39])([CH3:38])[CH2:23][C:22]=3[N:21]=[C:20]([CH:40]3[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]3)[C:19]=2[CH:46]([F:57])[C:47]2[CH:52]=[CH:51][C:50]([C:53]([F:56])([F:55])[F:54])=[CH:49][CH:48]=2)[CH2:14][CH2:13]1>>[F:58][C:12]1([F:11])[CH2:17][CH2:16][CH:15]([C:18]2[C:27]3[CH:26]([OH:28])[CH2:25][C:24]([CH3:38])([CH3:39])[CH2:23][C:22]=3[N:21]=[C:20]([CH:40]3[CH2:45][CH2:44][N:43]([C:2]4[N:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:4][N:3]=4)[CH2:42][CH2:41]3)[C:19]=2[CH:46]([F:57])[C:47]2[CH:52]=[CH:51][C:50]([C:53]([F:55])([F:56])[F:54])=[CH:49][CH:48]=2)[CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 198466722-Chloro-5-isopropylpyrimidineHCID 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-tetrahydroquinoline

Product 1

HCID 866824294-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-2-{1-[5-(propan-2-yl)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-(propan-2-yl) pyrimidine instead of 5-bromo-2-chloropyrimidine, and from 96 mg (0.14 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, 47 mg of the title compound was obtained as a white solid (yield: 50%).

Sources & evidence

ORD record
ord-7ae8c363877848a2a45eee589a336d03
Source dataset
uspto-grants-2015_11
Patent number
US09187450B2

Reaction notes

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