HCID 66707374, compound → HCID 66707523, compound

HRID 1848358Notes

Reaction equation

HRID 1848358 reaction equation
C([O:5][C:6](=[O:26])[CH2:7][CH:8]([CH3:25])[C:9]([C:11]1[N:16]2[N:17]=[C:18]([CH:20]3[CH2:22][CH2:21]3)[N:19]=[C:15]2[C:14]([O:23][CH3:24])=[CH:13][CH:12]=1)=[O:10])(C)(C)C>FC(F)(F)C(O)=O>[CH:20]1([C:18]2[N:19]=[C:15]3[C:14]([O:23][CH3:24])=[CH:13][CH:12]=[C:11]([C:9](=[O:10])[CH:8]([CH3:25])[CH2:7][C:6]([OH:26])=[O:5])[N:16]3[N:17]=2)[CH2:22][CH2:21]1

Participants

3

Reactant 1

HCID 66707374HCID 66707374, compound

Product 1

HCID 66707523HCID 66707523, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Under an argon atmosphere 4-(2-Cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-3-methyl-4-oxo-butyric acid tert-butyl ester (0.29 g) was dissolved in Trifluoroacetic acid (0.6 mL) and stirred at RT for 2 h after which the mixture was concentrated in vacuo. The crude product was suspended in 1 N NaOH (5 mL) and washed with Et2O (×2). The aqueous phase was adjusted to pH 1 with 4N HCl (1.5 mL) The aqueous phase was extracted with DCM (×2). The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo to afford 4-(2-Cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-3-methyl-4-oxo-butyric acid as a crude product.

Workup

  1. concentrationwas concentrated in vacuo
  2. washwashed with Et2O (×2)
  3. extractionwas extracted with DCM (×2)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-728911e32c904ca69276a1d50f94093b
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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