4-(4,4-Difluorocyclohexyl)-2-{1-[5-(ethoxymethyl)pyrimidin-2-yl]piperidin-4-yl}-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-5,6,7,8-tetrahydroquinoline → (-)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-2-(1-{5-[(propan-2-yloxy)methyl]pyrimidine-2-yl}piperidin-4-yl)-5,6,7,8-tetrahydroquinoline-5-ol

HRID 715868Notes

Reaction equation

HRID 715868 reaction equation
[F:1][C:2]1([F:59])[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[CH:16]([O:18]CC4C=CC(OC)=CC=4)[CH2:15][C:14]([CH3:29])([CH3:28])[CH2:13][C:12]=3[N:11]=[C:10]([CH:30]3[CH2:35][CH2:34][N:33]([C:36]4[N:41]=[CH:40][C:39]([CH2:42][O:43][CH:44]([CH3:46])[CH3:45])=[CH:38][N:37]=4)[CH2:32][CH2:31]3)[C:9]=2[CH:47]([F:58])[C:48]2[CH:53]=[CH:52][C:51]([C:54]([F:57])([F:56])[F:55])=[CH:50][CH:49]=2)[CH2:4][CH2:3]1.FC1(F)CCC(C2C3C(OCC4C=CC(OC)=CC=4)CC(C)(C)CC=3N=C(C3CCN(C4N=CC(COCC)=CN=4)CC3)C=2C(F)C2C=CC(C(F)(F)F)=CC=2)CC1>>[F:59][C:2]1([F:1])[CH2:3][CH2:4][CH:5]([C:8]2[C:17]3[CH:16]([OH:18])[CH2:15][C:14]([CH3:29])([CH3:28])[CH2:13][C:12]=3[N:11]=[C:10]([CH:30]3[CH2:35][CH2:34][N:33]([C:36]4[N:41]=[CH:40][C:39]([CH2:42][O:43][CH:44]([CH3:45])[CH3:46])=[CH:38][N:37]=4)[CH2:32][CH2:31]3)[C:9]=2[CH:47]([F:58])[C:48]2[CH:49]=[CH:50][C:51]([C:54]([F:55])([F:57])[F:56])=[CH:52][CH:53]=2)[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 866824354-(4,4-Difluorocyclohexyl)-2-{1-[5-(ethoxymethyl)pyrimidin-2-yl]piperidin-4-yl}-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-5,6,7,8-tetrahydroquinolineHCID 866824394-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-2-(1-{5-[(propan-2-yloxy)methyl]pyrimidin-2-yl}piperidin-4-yl)-5,6,7,8-tetrahydroquinoline

Product 1

HCID 86682438(-)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-2-(1-{5-[(propan-2-yloxy)methyl]pyrimidine-2-yl}piperidin-4-yl)-5,6,7,8-tetrahydroquinoline-5-olYield 67.7%

Procedure

Reactions similar to those of Example 26 were performed except for using 54 mg (0.065 mmol) of 4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-2-(1-{5-[(propan-2-yloxy)methyl]pyrimidin-2-yl}piperidin-4-yl)-5,6,7,8-tetrahydroquinoline, which was prepared by a method similar to that of Reference Example 23 instead of 4-(4,4-Difluorocyclohexyl)-2-{1-[5-(ethoxymethyl)pyrimidin-2-yl]piperidin-4-yl}-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-5,6,7,8-tetrahydroquinoline to provide 31 mg of the title compound as a white solid (yield: 67%).

Sources & evidence

ORD record
ord-d85c109c2240420aab663129bc2eaee0
Source dataset
uspto-grants-2015_11
Patent number
US09187450B2

Reaction notes

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