HCID 59278116, compound → HCID 59278281, compound

HRID 559682Notes

Reaction equation

HRID 559682 reaction equation
Br[C:2]1[S:3][C:4]([CH2:7][NH:8][C:9]([C:11]2[C:12]3[CH:19]=[N:18][N:17]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[C:13]=3[CH:14]=[N:15][CH:16]=2)=[O:10])=[CH:5][N:6]=1>C(OC(=O)C)(=O)C.[OH-].[Na+]>[C:9]([N:8]([CH3:7])[C:2]1[S:3][C:4]([CH2:7][NH:8][C:9]([C:11]2[C:12]3[CH:19]=[N:18][N:17]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[C:13]=3[CH:14]=[N:15][CH:16]=2)=[O:10])=[CH:5][N:6]=1)(=[O:10])[CH3:11]

Participants

4

Reactant 1

HCID 59278116HCID 59278116, compound

Product 1

HCID 59278281HCID 59278281, compound

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid (2-bromo-thiazol-5-ylmethyl)-amide (80 mg, 0.2 mmol) in acetic anhydride (2 mL) was heated at 60° C. for 18 hours. The solution was diluted with 10 mL of a 1 N solution of aqueous NaOH and stirred for 10 minutes. The solution was then extracted with dichloromethane (20 mL). The organic layers were dried over sodium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography eluting with a gradient of 0-10% methanol in dichloromethane. The purification was repeated eluting with a gradient of 0-7% methanol in dichloromethane. The material from the purification was diluted with dichloromethane (1 mL) followed by hexanes (5 mL). The solid was collected by filteration to afford the title compound.

Workup

  1. extractionThe solution was then extracted with dichloromethane (20 mL)
  2. dry with materialThe organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by silica gel chromatography
  6. washeluting with a gradient of 0-10% methanol in dichloromethane
  7. customThe purification
  8. washwas repeated eluting with a gradient of 0-7% methanol in dichloromethane
  9. customThe material from the purification
  10. additionwas diluted with dichloromethane (1 mL)
  11. customThe solid was collected by filteration

Sources & evidence

ORD record
ord-dd7425863f874570a0457c42f275ccc9
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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