Sodium Hydroxide → HCID 68295778, compound

HRID 1909343Notes

Reaction equation

HRID 1909343 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]([C:28]([O:30]C)=[O:29])[C:17]3[CH:18]=[N:19][N:20]([CH:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)[C:21]=3[CH:22]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:15]=[C:16]([C:28]([OH:30])=[O:29])[C:17]3[CH:18]=[N:19][N:20]([CH:23]4[CH2:24][CH2:25][CH2:26][CH2:27]4)[C:21]=3[CH:22]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68294895methyl 6-(4-(tert-butoxycarbonyl)piperazin-1-yl)-1-cyclopentyl-1H-indazole-4-carboxylate

Product 1

HCID 68295778HCID 68295778, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of methyl 6-(4-(tert-butoxycarbonyl)piperazin-1-yl)-1-cyclopentyl-1H-indazole-4-carboxylate (2 g, 4.67 mmol) in methanol (20 mL), was added aqueous NaOH solution (0.373 g, dissolved in 10 mL water, 9.34 mmol) and the reaction mixture stirred at 60° C. for 4 h. On completion, ethanol was removed under reduced pressure and the residue acidified with 1N HCl to pH 6. The precipitate was filtered, washed with water and dried to obtain pure 6-(4-(tert-butoxycarbonyl)piperazin-1-yl)-1-cyclopentyl-1H-indazole-4-carboxylic acid (1.7 g, 88%).

Workup

  1. customOn completion, ethanol was removed under reduced pressure
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-98a88897346643258d4e635501247017
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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