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

HRID 60985Notes

Reaction equation

HRID 60985 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[C:53]1[N:57]([CH3:58])[N:56]=[CH:55][CH:54]=1)=[O:45].Cl[C:60]1[CH:67]=[CH:66][C:63]([C:64]#[N:65])=[CH:62][N:61]=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[C:53]2[N:57]([CH3:58])[N:56]=[CH:55][CH:54]=2)[C@@H:37]1[CH2:36][NH:35][C:60]1[CH:67]=[CH:66][C:63]([C:64]#[N:65])=[CH:62][N:61]=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 117727777((2S,3R)-2-(Aminomethyl)-3-methylpiperidin-1-yl)(5-methyl-2-(1-methyl-1H-pyrazol-5-yl)phenyl)methanone

Product 1

HCID 1177280576-((((2S,3R)-3-Methyl-1-(5-methyl-2-(1-methyl-1H-pyrazol-5-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-(1-methyl-1H-pyrazol-5-yl)phenyl)methanone and 6-chloronicotinonitrile. ESI-MS (m/z): 429 [M+1]+.

Sources & evidence

ORD record
ord-d150d22b9eaa43c9a4ffe0915a792305
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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