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

HRID 517940Notes

Reaction equation

HRID 517940 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:34]=[CH:33][C:16]([O:17][CH2:18][CH2:19][CH:20]3[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]3)=[C:15]([C:35]([F:38])([F:37])[F:36])[CH:14]=2)[N:4]=1)#[N:2].[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]>C(Cl)Cl.C(#N)C>[OH:45][C:39]([C:41]([F:44])([F:43])[F:42])=[O:40].[CH3:12][N:11]1[C:7]2[CH:6]=[C:5]([C:13]3[CH:34]=[CH:33][C:16]([O:17][CH2:18][CH2:19][CH:20]4[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]4)=[C:15]([C:35]([F:38])([F:37])[F:36])[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 67294242HCID 67294242, compound

Product 1

HCID 866733471-methyl-6-(4-(2-(piperidin-4-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile 2,2,2-trifluoroacetate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 4-(2-(4-(4-cyano-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)ethyl)piperidine-1-carboxylate (6 g) in DCM (40 ml) and acetonitrile (20 ml) was added TFA (40 ml). The mixture was stirred at room temperature for 10 minutes, then solvent removed under vacuum. To the residue was then dissolved ethyl acetate (40 ml) and product was precipitated by adding ether (50 ml) and collected by filtration (6.05 g as TFA salt).

Workup

  1. customsolvent removed under vacuum
  2. customdissolved ethyl acetate (40 ml) and product was precipitated
  3. additionby adding ether (50 ml)
  4. filtrationcollected by filtration (6.05 g as TFA salt)

Sources & evidence

ORD record
ord-37936b6326b84110bbf50dd0bb15b5e2
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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