2-Bromo-3-fluoro-5-(trifluoromethyl)pyridine → ((2S,3R)-2-(((3-Fluoro-5-(trifluoromethyl)pyridin-2-yl)amino)methyl)-3-methylpiperidin-1-yl)(5-methyl-2-(1-methyl-1H-pyrazol-4-yl)phenyl)methanone

HRID 61012Notes

Reaction equation

HRID 61012 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=2[C:17]2[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=2)=[O:9])[C@@H:3]1[CH2:23][NH:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=1.BrC1C([F:42])=CC(C(F)(F)F)=CN=1>>[F:42][C:30]1[C:25]([NH:24][CH2:23][C@@H:3]2[C@H:2]([CH3:1])[CH2:7][CH2:6][CH2:5][N:4]2[C:8]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=2[C:17]2[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=2)=[O:9])=[N:26][CH:27]=[C:28]([C:31]([F:34])([F:32])[F:33])[CH:29]=1

Participants

3

Reactant 2

HCID 155928232-Bromo-3-fluoro-5-(trifluoromethyl)pyridineHCID 89748276rac-((2S,3R)-3-methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)(5-methyl-2-(1-methyl-1H-pyrazol-4-yl)phenyl)methanone

Product 1

HCID 117727700((2S,3R)-2-(((3-Fluoro-5-(trifluoromethyl)pyridin-2-yl)amino)methyl)-3-methylpiperidin-1-yl)(5-methyl-2-(1-methyl-1H-pyrazol-4-yl)phenyl)methanone

Procedure

The title compound was synthesized following the same general protocol as described for ((2S,3R)-3-methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)(5-methyl-2-(1-methyl-1H-pyrazol-4-yl)phenyl)methanone in Example A1, using 2-bromo-3-fluoro-5-(trifluoromethyl)pyridine. ESI-MS (m/z): 490 [M+1]+.

Sources & evidence

ORD record
ord-d918e9e0cbfe45d3872bcaa4d0796848
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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