Sodium Hydroxide → N-(4-hydroxymethylcyclohexyl)-1H-indazole-5-carboxamide

HRID 1269759Notes

Reaction equation

HRID 1269759 reaction equation
[BH4-].[Li+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([NH:14][CH:15]3[CH2:20][CH2:19][CH:18]([C:21](OC)=[O:22])[CH2:17][CH2:16]3)=[O:13])=[CH:9][CH:10]=2)[CH:5]=[N:4]1.[OH-].[Na+]>O1CCCC1>[OH:22][CH2:21][CH:18]1[CH2:19][CH2:20][CH:15]([NH:14][C:12]([C:8]2[CH:7]=[C:6]3[C:11](=[CH:10][CH:9]=2)[NH:3][N:4]=[CH:5]3)=[O:13])[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 18447321methyl 4-[(1H-indazol-5-ylcarbonyl)amino]cyclohexanecarboxylate

Product 1

HCID 22934019N-(4-hydroxymethylcyclohexyl)-1H-indazole-5-carboxamideYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium borohydride (10.0 mg, 0.459 mmol) was added to a solution of the methyl 4-[(1H-indazol-5-ylcarbonyl)amino]cyclohexanecarboxylate (30.0 mg, 0.0951 mmol) obtained in Example 186 in tetrahydrofuran (3.0 ml) at room temperature, and the resulting mixture was stirred for 2 hours with heating under reflux while maintaining the temperature. A 1N aqueous sodium hydroxide solution (0.8 ml) was added to the reaction solution, and the resulting mixture was stirred while being maintained at room temperature, and then was concentrated to dryness. The resulting crude product residue was stirred in methanol (3.0 ml) for another 1 hour with heating under reflux while maintaining the temperature. The resulting mixture was concentrated to dryness and purified by a silica gel column chromatography (eluent: chloroform/methanol=20/1) to obtain N-(4-hydroxymethylcyclohexyl)-1H-indazole-5-carboxamide (23.5 mg, 91%).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. temperaturewhile maintaining the temperature
  4. stirringthe resulting mixture was stirred
  5. concentrationwas concentrated to dryness
  6. stirringThe resulting crude product residue was stirred in methanol (3.0 ml) for another 1 hour
  7. temperaturewith heating
  8. temperatureunder reflux
  9. temperaturewhile maintaining the temperature
  10. concentrationThe resulting mixture was concentrated to dryness
  11. custompurified by a silica gel column chromatography (eluent: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-d6d891b5902e46d88a6533d3ea243c93
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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