Acetic Acid → 4-Amino-6-chloro-2-(4-methoxyphenyl)methyl-2H-pyrazolo[3,4-b]pyridine-5-carboxylic Acid

HRID 478597Notes

Reaction equation

HRID 478597 reaction equation
C([O:3][C:4]([C:6]1[C:11]([Cl:12])=[N:10][C:9]2=[N:13][N:14]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH:15]=[C:8]2[C:7]=1[NH2:25])=[O:5])C.CO.C1COCC1.CC(O)=O>[OH-].[Na+]>[NH2:25][C:7]1[C:8]2[C:9](=[N:13][N:14]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH:15]=2)[N:10]=[C:11]([Cl:12])[C:6]=1[C:4]([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 21899815MeOH tetrahydrofuranHCID 59912879HCID 59912879, compound

Product 1

HCID 180024944-Amino-6-chloro-2-(4-methoxyphenyl)methyl-2H-pyrazolo[3,4-b]pyridine-5-carboxylic AcidYield 101.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4-amino-6-chloro-2-(4-methoxyphenyl)methyl-2H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (800 mg) in NaOH (1N)/MeOH/THF (1:1:1, 15 mL) was stirred for 4 days. The acidity of the reaction mixture was adjusted to pH 5-6 with AcOH. The THF and MeOH were removed. The residue was dissolved in water (30 mL) then extracted with EtOAc (3×100 mL). The combined extracts were dried (NaSO4). Removal of the solvent gave the desired product (746 mg) as white solid. LC: 3.13 (Gradient 1), MH+: 333

Workup

  1. customThe THF and MeOH were removed
  2. dissolutionThe residue was dissolved in water (30 mL)
  3. extractionthen extracted with EtOAc (3×100 mL)
  4. dry with materialThe combined extracts were dried (NaSO4)
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-959b9d1c24b24764a266c0e9cabb5dba
Source dataset
uspto-grants-2003_11
Patent number
US06642244B2

Reaction notes

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