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

HRID 715857Notes

Reaction equation

HRID 715857 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:4][N:3]=1.[F:13][C:14]1([F:60])[CH2:19][CH2:18][CH:17]([C:20]2[C:29]3[CH:28]([O:30]CC4C=CC(OC)=CC=4)[CH2:27][C:26]([CH3:41])([CH3:40])[CH2:25][C:24]=3[N:23]=[C:22]([CH:42]3[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]3)[C:21]=2[CH:48]([F:59])[C:49]2[CH:54]=[CH:53][C:52]([C:55]([F:58])([F:57])[F:56])=[CH:51][CH:50]=2)[CH2:16][CH2:15]1>>[F:60][C:14]1([F:13])[CH2:19][CH2:18][CH:17]([C:20]2[C:29]3[CH:28]([OH:30])[CH2:27][C:26]([CH3:40])([CH3:41])[CH2:25][C:24]=3[N:23]=[C:22]([CH:42]3[CH2:47][CH2:46][N:45]([C:2]4[N:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:4][N:3]=4)[CH2:44][CH2:43]3)[C:21]=2[CH:48]([F:59])[C:49]2[CH:54]=[CH:53][C:52]([C:55]([F:57])([F:58])[F:56])=[CH:51][CH:50]=2)[CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 167565262-Chloro-5-pentylpyrimidineHCID 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 76372414(-)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-2-[1-(5-pentylpyrimidin-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-pentyl pyrimidine instead of 5-bromo-2-chloropyrimidine, and from 100 mg (0.148 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, 95 mg of the title compound was obtained as a white solid (yield: 91%).

Sources & evidence

ORD record
ord-60f8b71d8e31484bb097d4e278a2ad0f
Source dataset
uspto-grants-2015_11
Patent number
US09187450B2

Reaction notes

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