Water → HCID 22933967, compound

HRID 1269804Notes

Reaction equation

HRID 1269804 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH:17]3[CH2:22][CH2:21][CH:20]([C:23]([NH2:25])=O)[CH2:19][CH2:18]3)=[CH:13][CH:14]=2)[CH:9]=[N:8]1.O.[OH-].[Na+]>O1CCCC1>[NH:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH:17]3[CH2:18][CH2:19][CH:20]([CH2:23][NH2:25])[CH2:21][CH2:22]3)=[CH:13][CH:14]=2)[CH:9]=[N:8]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22933871HCID 22933871, compound

Product 1

HCID 22933967HCID 22933967, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (58 mg, 1.54 mmol) was added to a solution of the 4-(1H-indazol-5-yloxy)cyclohexanecarboxamide (100 mg, 0.386 mmol) obtained in Example 369 in tetrahydrofuran (3 ml), and the resulting mixture was refluxed. After 6 hours, water (0.087 ml), a 2M-aqueous sodium hydroxide solution (0.176 ml) and then water (0.261 ml) were added to the reaction mixture, and the resulting solution was filtered by the use of Celite. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol→chloroform/methanol (1%-aqueous ammonia)) to obtain 1-[4-(1H-indazol-5-yloxy)cyclohexyl]methanamine (49 mg, 52%).

Workup

  1. temperaturethe resulting mixture was refluxed
  2. filtrationthe resulting solution was filtered by the use of Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol→chloroform/methanol (1%-aqueous ammonia))

Sources & evidence

ORD record
ord-5cc0b2c3eb954624a2ebf13bae6ee521
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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