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

HRID 517983Notes

Reaction equation

HRID 517983 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:32]=[CH:31][C:16]([O:17][CH2:18][CH2:19][CH:20]3[CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]3)=[C:15]([C:33]([F:36])([F:35])[F:34])[CH:14]=2)[N:4]=1)#[N:2].[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40]>C(Cl)Cl.C(#N)C>[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40].[NH:22]1[CH2:23][CH:20]([CH2:19][CH2:18][O:17][C:16]2[CH:31]=[CH:32][C:13]([C:5]3[N:4]=[C:3]([C:1]#[N:2])[C:8]4[N:9]=[N:10][N:11]([CH3:12])[C:7]=4[CH:6]=3)=[CH:14][C:15]=2[C:33]([F:36])([F:34])[F:35])[CH2:21]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67294315tert-butyl 3-(2-(4-(4-cyano-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)ethyl)azetidine-1-carboxylate

Product 1

HCID 866733526-(4-(2-(azetidin-3-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile 2,2,2-trifluoroacetateYield 62%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-(2-(4-(4-cyano-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)ethyl)azetidine-1-carboxylate (86 mg) was dissolved in DCM (2000 μl) and acetonitrile (500 μl). Trifluoroacetic acid (400 μl) was added and the reaction stirred for 30 minutes. Solvent was evaporated under reduced pressure and the resulting residue dissolved in a minimum volume of EtOAc. Ether was added dropwise until the solution clouded then the mixture was allowed to stand for 30 minutes and filtered. Solid was washed with ether and dried to afford the desired product 6-(4-(2-(azetidin-3-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile 2,2,2-trifluoroacetate (62% yield).

Workup

  1. customSolvent was evaporated under reduced pressure
  2. dissolutionthe resulting residue dissolved in a minimum volume of EtOAc
  3. additionEther was added dropwise until the solution
  4. waitto stand for 30 minutes
  5. filtrationfiltered
  6. washSolid was washed with ether
  7. customdried

Sources & evidence

ORD record
ord-94056b3c3a9e4a8e8458977bb5bdc950
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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