2-Chloro-5-(difluoromethoxy)pyrimidine → HCID 86682465, compound

HRID 715883Notes

Reaction equation

HRID 715883 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([O:8][CH:9]([F:11])[F:10])=[CH:4][N:3]=1.ClC1N=CC(OC2CCN(C)CC2)=CN=1.[F:27][C:28]1([F:74])[CH2:33][CH2:32][CH:31]([C:34]2[C:43]3[CH:42]([O:44]CC4C=CC(OC)=CC=4)[CH2:41][C:40]([CH3:55])([CH3:54])[CH2:39][C:38]=3[N:37]=[C:36]([CH:56]3[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]3)[C:35]=2[CH:62]([F:73])[C:63]2[CH:68]=[CH:67][C:66]([C:69]([F:72])([F:71])[F:70])=[CH:65][CH:64]=2)[CH2:30][CH2:29]1>>[F:74][C:28]1([F:27])[CH2:33][CH2:32][CH:31]([C:34]2[C:43]3[CH:42]([OH:44])[CH2:41][C:40]([CH3:54])([CH3:55])[CH2:39][C:38]=3[N:37]=[C:36]([CH:56]3[CH2:61][CH2:60][N:59]([C:2]4[N:7]=[CH:6][C:5]([O:8][CH:9]([F:11])[F:10])=[CH:4][N:3]=4)[CH2:58][CH2:57]3)[C:35]=2[CH:62]([F:73])[C:63]2[CH:68]=[CH:67][C:66]([C:69]([F:71])([F:72])[F:70])=[CH:65][CH:64]=2)[CH2:30][CH2:29]1

Participants

4

Reactant 3

HCID 574765572-Chloro-5-(difluoromethoxy)pyrimidineHCID 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-tetrahydroquinolineHCID 866824592-Chloro-5-[(1-methylpiperidin-4-yl)oxy]pyrimidine

Product 1

HCID 86682465HCID 86682465, compound

Procedure

Reactions similar to those of Reference Example 29 and Example 38 were performed except for using 2-chloro-5-(difluoromethoxy)pyrimidine, which was prepared by a method similar to that of Reference Example 32, instead of 2-chloro-5-[(1-methylpiperidin-4-yl)oxy]pyrimidine, and from 102 mg (151 μmol) 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, 52 mg of the title compound was obtained as a white solid (yield: 49%).

Workup

  1. customwas prepared by a method similar to that of Reference Example 32

Sources & evidence

ORD record
ord-38a8493eb3d34023ad8df8bedead4093
Source dataset
uspto-grants-2015_11
Patent number
US09187450B2

Reaction notes

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