Water → 2-(1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-6-ylamino)acetic acid

HRID 402481Notes

Reaction equation

HRID 402481 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][C:8]([NH:15][CH2:16][C:17]([O:19]C)=[O:18])=[CH:9][C:10]([C:11]([F:14])([F:13])[F:12])=[C:5]2[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:3]1.O>C(O)C.[Li+].[OH-]>[CH3:1][N:2]1[C:6]2=[N:7][C:8]([NH:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:9][C:10]([C:11]([F:13])([F:14])[F:12])=[C:5]2[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:3]1

Participants

5

Reactant 2

HCID 962WaterHCID 67209395methyl 2-(1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-6-ylamino)acetate

Product 1

HCID 672095372-(1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-6-ylamino)acetic acidYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3939Lithium HydroxideSolvent

Procedure

To a solution of methyl 2-(1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-6-ylamino)acetate (0.045 g, 0.123 mmol) in ethanol (2.0 mL), aqueous LiOH×H2O (0.026 g, 0.618 mmol in 0.1 mL) was added and stirred at it for 15 min. The organic solvents were removed under reduced pressure and the reaction mixture was acidified with 10% HCl (pH ˜2) to obtain a white solid which was filtered through a funnel and dried under vacuum to yield the title compound as a white solid (0.036 g, 90%). [1H-NMR (DMSO-d6, 300 MHz) δ 7.99 (s, 1H), 7.45-7.38 (m, 5H), 6.85 (s, 1H), 4.15 (d, 2H), 3.92 (s, 3H); LCMS RtC=0.39 min; [M+H]+=351.1]

Workup

  1. customThe organic solvents were removed under reduced pressure
  2. customto obtain a white solid which
  3. filtrationwas filtered through a funnel
  4. customdried under vacuum

Sources & evidence

ORD record
ord-491edd48cf3c42ab8a64934a52a28b1f
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

Loading…