Trifluoroacetic acid → HCID 59419628, compound

HRID 1670731Notes

Reaction equation

HRID 1670731 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[C:21](=O)([O-])[O-].[K+].[K+].[NH2:27][NH2:28].C(O)(C(F)(F)F)=O>>[N:27]1[N:28]=[CH:21][N:7]2[CH:6]=[C:5]([CH:8]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=[O:11])[CH:4]=[CH:3][C:2]=12

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 9321HydrazineHCID 11430Potassium CarbonateHCID 59138622HCID 59138622, compound

Product 1

HCID 59419628HCID 59419628, compoundYield 81%

Conditions

Temperature
110 °C

Procedure

A mixture of 3-(6-chloropyridin-3-yl)-2,2-dimethyl-3-phenylpropanoic acid (28 mg, 0.10 mmol), potassium carbonate (8 mg), and hydrazine (0.5 mL) was stirred at 110° C. for 11 hr under argon and then concentrated. The residue was mixed with formic acid (1 mL). The mixture was stirred at 100° C. for 2 hr and 120° C. for 1 hr. Concentration and purification using reverse phase HPLC (YMC S5 20×100 mm, 10 min. run, solvent A: 10% MeOH: 90% H2O: 0.1% TFA, solvent B: 90% MeOH, 10% H2O, 0.1% TFA) gave 3-([1,2,4]triazolo[4,3-a]pyridin-6-yl)-2,2-dimethyl-3-phenylpropanoic acid (33 mg, 0.081 mmol, 81% yield) as a TFA salt. MS found: (M+H)+=296.25.

Workup

  1. concentrationconcentrated
  2. additionThe residue was mixed with formic acid (1 mL)
  3. stirringThe mixture was stirred at 100° C. for 2 hr and 120° C. for 1 hr
  4. concentrationConcentration and purification
  5. customphase HPLC (YMC S5 20×100 mm, 10 min. run, solvent A: 10% MeOH: 90% H2O: 0.1% TFA, solvent B: 90% MeOH, 10% H2O, 0.1% TFA)

Sources & evidence

ORD record
ord-86f6fbeebf2d492296d63e96e6dd182f
Source dataset
uspto-grants-2011_08
Patent number
US07994190B2

Reaction notes

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