6-Chloro-3-pyridinecarbonitrile → 6-((((2S,3R)-3-Methyl-1-(5-methyl-2-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)benzoyl)piperidin-2-yl)methyl)amino)nicotinonitrile

HRID 60970Notes

Reaction equation

HRID 60970 reaction equation
C[C@@H]1CCCN(C(C2C=C(C)C=CC=2C2C=NN(C)C=2)=O)[C@@H]1CNC1C=CC(C(F)(F)F)=CN=1.[NH2:35][CH2:36][C@@H:37]1[C@H:42]([CH3:43])[CH2:41][CH2:40][CH2:39][N:38]1[C:44]([C:46]1[CH:51]=[C:50]([CH3:52])[CH:49]=[CH:48][C:47]=1[N:53]1[CH:57]=[N:56][C:55]([C:58]([F:61])([F:60])[F:59])=[N:54]1)=[O:45].Cl[C:63]1[CH:70]=[CH:69][C:66]([C:67]#[N:68])=[CH:65][N:64]=1>>[CH3:43][C@@H:42]1[CH2:41][CH2:40][CH2:39][N:38]([C:44](=[O:45])[C:46]2[CH:51]=[C:50]([CH3:52])[CH:49]=[CH:48][C:47]=2[N:53]2[CH:57]=[N:56][C:55]([C:58]([F:61])([F:60])[F:59])=[N:54]2)[C@@H:37]1[CH2:36][NH:35][C:63]1[CH:70]=[CH:69][C:66]([C:67]#[N:68])=[CH:65][N:64]=1

Participants

4

Reactant 3

HCID 51520946-Chloro-3-pyridinecarbonitrileHCID 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)methanoneHCID 117727731((2S,3R)-2-(aminomethyl)-3-methylpiperidin-1-yl)(5-methyl-2-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)phenyl)methanone

Product 1

HCID 1177278546-((((2S,3R)-3-Methyl-1-(5-methyl-2-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)benzoyl)piperidin-2-yl)methyl)amino)nicotinonitrile

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 ((2S,3R)-2-(aminomethyl)-3-methylpiperidin-1-yl)(5-methyl-2-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)phenyl)methanone and 6-chloronicotinonitrile. ESI-MS (m/z): 484 [M+1]+.

Sources & evidence

ORD record
ord-f300c650eaf441aeb1b4422219284998
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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