Trifluoroacetic acid → 1-methyl-6-(6-(2-(piperidin-4-yl)ethoxy)-5-(trifluoromethyl)pyridin-3-yl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile trifluoroacetate

HRID 517975Notes

Reaction equation

HRID 517975 reaction equation
[C:1]([C:3]1[C:8]2[N:9]=[N:10][N:11]([CH3:12])[C:7]=2[CH:6]=[C:5]([C:13]2[CH:14]=[C:15]([C:35]([F:38])([F:37])[F:36])[C:16]([O:19][CH2:20][CH2:21][CH:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)=[N:17][CH:18]=2)[N:4]=1)#[N:2].[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42]>ClCCl.C(#N)C>[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42].[CH3:12][N:11]1[C:7]2[CH:6]=[C:5]([C:13]3[CH:18]=[N:17][C:16]([O:19][CH2:20][CH2:21][CH:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)=[C:15]([C:35]([F:36])([F:37])[F:38])[CH:14]=3)[N:4]=[C:3]([C:1]#[N:2])[C:8]=2[N:9]=[N:10]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70945099HCID 70945099, compound

Product 1

HCID 866733511-methyl-6-(6-(2-(piperidin-4-yl)ethoxy)-5-(trifluoromethyl)pyridin-3-yl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile trifluoroacetateYield 78%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of tert-butyl 4-(2-(5-(4-cyano-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)-3-(trifluoromethyl)pyridin-2-yloxy)ethyl)piperidine-1-carboxylate (1.15 g) in dichloromethane (10 ml) and acetonitrile (5 ml), trifluoroacetic acid (2 ml) was added and the mixture stirred at 20° C. for 1 h then solvent evaporated under reduced pressure. The resulting residue was dissolved in ethyl acetate (10 ml) and diethyl ether added dropwise until the mixture turned cloudy. The solution was allowed to stand for two hours. The desired product was collected by filtration and washed with ether, dried in vacuum oven to give 920 mg 1-methyl-6-(6-(2-(piperidin-4-yl)ethoxy)-5-(trifluoromethyl)pyridin-3-yl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile trifluoroacetate (78%).

Workup

  1. customsolvent evaporated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in ethyl acetate (10 ml)
  3. additiondiethyl ether added dropwise until the mixture
  4. waitto stand for two hours
  5. filtrationThe desired product was collected by filtration
  6. washwashed with ether
  7. customdried in vacuum oven

Sources & evidence

ORD record
ord-19ebbbcb137b4839bc3c23d211e28a88
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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