Methyl iodide → ((2S,3R)-3-Methyl-2-((methyl(5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)(6-methyl-3-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)methanone

HRID 61123Notes

Reaction equation

HRID 61123 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([C:10]2[C:15]([N:16]3[N:20]=[CH:19][CH:18]=[N:17]3)=[CH:14][CH:13]=[C:12]([CH3:21])[N:11]=2)=[O:9])[C@@H:3]1[CH2:22][NH:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][N:25]=1.[H-].[Na+].[CH3:36]I>CN(C=O)C>[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([C:10]2[C:15]([N:16]3[N:17]=[CH:18][CH:19]=[N:20]3)=[CH:14][CH:13]=[C:12]([CH3:21])[N:11]=2)=[O:9])[C@@H:3]1[CH2:22][N:23]([CH3:36])[C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:31])[F:32])=[CH:26][N:25]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 117728080((2S,3R)-3-Methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)(6-methyl-3-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)methanone

Product 1

HCID 117727658((2S,3R)-3-Methyl-2-((methyl(5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)(6-methyl-3-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ((2S,3R)-3-methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)(6-methyl-3-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)methanone (0.0215 g, 0.047 mmol) in DMF (0.5 mL) at rt was added NaH (60%, 0.006 g, 0.141 mmol). The mixture was stirred at rt for 1 h, then MeI (0.013 g, 0.094 mmol) was added. The reaction was stirred at rt for another 1 h. The crude was purified via preparative-HPLC to obtain the title compound. ESI-MS (m/z): 474 [M+1]+.

Workup

  1. stirringThe reaction was stirred at rt for another 1 h
  2. customThe crude was purified via preparative-HPLC

Sources & evidence

ORD record
ord-9fd9e919cf36453a92011af2f1d6af1c
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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