6-Chloro-5-fluoronicotinonitrile → 5-Fluoro-6-((((2S,3R)-3-methyl-1-(6-methyl-3-(2H-1,2,3-triazol-2-yl)picolinoyl)piperidin-2-yl)methyl)amino)nicotinonitrile

HRID 61122Notes

Reaction equation

HRID 61122 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[C:17]([N:18]2[N:22]=[CH:21][CH:20]=[N:19]2)=[CH:16][CH:15]=[C:14]([CH3:23])[N:13]=1)=[O:11].Cl[C:25]1[C:32]([F:33])=[CH:31][C:28]([C:29]#[N:30])=[CH:27][N:26]=1>>[F:33][C:32]1[C:25]([NH:1][CH2:2][C@@H:3]2[C@H:8]([CH3:9])[CH2:7][CH2:6][CH2:5][N:4]2[C:10](=[O:11])[C:12]2[C:17]([N:18]3[N:22]=[CH:21][CH:20]=[N:19]3)=[CH:16][CH:15]=[C:14]([CH3:23])[N:13]=2)=[N:26][CH:27]=[C:28]([CH:31]=1)[C:29]#[N:30]

Participants

3

Reactant 2

HCID 467386836-Chloro-5-fluoronicotinonitrileHCID 117727634((2S,3R)-2-(Aminomethyl)-3-methylpiperidin-1-yl)(6-methyl-3-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)methanone

Product 1

HCID 1177281615-Fluoro-6-((((2S,3R)-3-methyl-1-(6-methyl-3-(2H-1,2,3-triazol-2-yl)picolinoyl)piperidin-2-yl)methyl)amino)nicotinonitrile

Procedure

The title compound was prepared following the same general protocol as described for Example A1, using ((2S,3R)-2-(aminomethyl)-3-methylpiperidin-1-yl)(6-methyl-3-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)methanone and 6-chloro-5-fluoronicotinonitrile. ESI-MS (m/z): 435 [M+1]+.

Sources & evidence

ORD record
ord-05d5e800ad904961b4155549e1933b47
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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