Water → {[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]amino}-acetic acid methyl ester

HRID 2198153Notes

Reaction equation

HRID 2198153 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[N:14][CH:15]=[C:16]([C:17]([OH:19])=O)[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH3:33][O:34][C:35](=[O:38])[CH2:36][NH2:37].O>CN(C=O)C.C(=O)(O)[O-].[NH4+]>[CH3:33][O:34][C:35](=[O:38])[CH2:36][NH:37][C:17]([C:16]1[C:11]2[CH:10]=[N:9][N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:12]=2[CH:13]=[N:14][CH:15]=1)=[O:19]

Participants

7

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 122755Glycine methyl ester hydrochlorideHCID 592781371-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid

Product 1

HCID 66727434{[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]amino}-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 14013Ammonium BicarbonateSolvent

Procedure

A suspension of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid (2.95 g, 11.5 mmol) in DMF (25 mL) was treated with CDI (1.51 g, 12.0 mmol). The mixture turned to a dark brown clear solution in 5 minutes, and then a solid precipitate formed. Additional DMF (10 mL) was added to assist stirring. The mixture was stirred for 1 hour. A solution of glycine methyl ester hydrochloride (2.42 g, 14.9 mmol) in DMF (5 mL) was added. After 18 hours, the mixture was poured into water (200 mL) and diluted with saturated aqueous ammonium bicarbonate (50 mL). The solid was collected by filtration to afford {[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-acetic acid methyl ester as a light brown solid.

Workup

  1. customa solid precipitate formed
  2. stirringThe mixture was stirred for 1 hour
  3. waitAfter 18 hours
  4. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-53b0280e2f4e4dca9cac2ebaf686440c
Source dataset
uspto-grants-2012_12
Patent number
US08338610B2

Reaction notes

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