2-Chloro-5-(trifluoromethyl)pyrimidine → ((2S,3R)-3-Methyl-2-(((5-(trifluoromethyl)pyrimidin-2-yl)amino)methyl)piperidin-1-yl)(2-(pyrimidin-2-yl)phenyl)methanone

HRID 61250Notes

Reaction equation

HRID 61250 reaction equation
[NH2:1][CH2:2][C@@H:3]1[C@H:8]([CH3:9])[CH2:7][CH2:6][CH2:5][N:4]1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1)=[O:11].Cl[C:25]1[N:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=1>>[CH3:9][C@@H:8]1[CH2:7][CH2:6][CH2:5][N:4]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]2[N:19]=[CH:20][CH:21]=[CH:22][N:23]=2)=[O:11])[C@@H:3]1[CH2:2][NH:1][C:25]1[N:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=1

Participants

3

Reactant 2

HCID 133170192-Chloro-5-(trifluoromethyl)pyrimidineHCID 117727638((2S,3R)-2-(aminomethyl)-3-methylpiperidin-1-yl)(2-(pyrimidin-2-yl)phenyl)methanone

Product 1

HCID 117727684((2S,3R)-3-Methyl-2-(((5-(trifluoromethyl)pyrimidin-2-yl)amino)methyl)piperidin-1-yl)(2-(pyrimidin-2-yl)phenyl)methanone

Procedure

The title compound was prepared following the same general protocol as described for Example A316 using ((2S,3R)-2-(aminomethyl)-3-methylpiperidin-1-yl)(2-(pyrimidin-2-yl)phenyl)methanone and 2-chloro-5-(trifluoromethyl)pyrimidine. ESI-MS (m/z): 457 [M+1]+. 1H NMR (500 MHz, CD3OD) δ 9.05-6.85 (m, 9H), 5.15-3.00 (m, 5H), 2.10-0.75 (m, 8H).

Sources & evidence

ORD record
ord-46c47441d40b49cdb893ae9ec9d62e86
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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