Trifluoroacetic acid → {6-[(2'-cyanobiphenyl-4-yl)methyl]-5-oxo-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-4(5H)-yl}acetic acid

HRID 2062376Notes

Reaction equation

HRID 2062376 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]2[C:17](=[O:36])[N:18]([CH2:28][C:29]([O:31]C(C)(C)C)=[O:30])[C:19]3[N:20]([N:25]=[CH:26][N:27]=3)[C:21]=2[CH2:22][CH2:23][CH3:24])=[CH:11][CH:10]=1)#[N:2].FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]2[C:17](=[O:36])[N:18]([CH2:28][C:29]([OH:31])=[O:30])[C:19]3[N:20]([N:25]=[CH:26][N:27]=3)[C:21]=2[CH2:22][CH2:23][CH3:24])=[CH:13][CH:14]=1)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86644024tert-butyl {6-[(2'-cyanobiphenyl-4-yl)methyl]-5-oxo-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-4(5H)-yl}acetate

Product 1

HCID 67008414{6-[(2'-cyanobiphenyl-4-yl)methyl]-5-oxo-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-4(5H)-yl}acetic acidYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of tert-butyl {6-[(2′-cyanobiphenyl-4-yl)methyl]-5-oxo-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-4(5H)-yl}acetate (1.78 g) and trifluoroacetic acid (15 mL) was stirred at room temperature for 1 hr. The reaction mixture was diluted with toluene (15 mL) and the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (1.44 g, 92%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f5a8fc17b4534b9bbba1a4e496687985
Source dataset
uspto-grants-2012_10
Patent number
US08283353B2

Reaction notes

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