Tetrahydrofuran → HCID 18447189, compound

HRID 1269832Notes

Reaction equation

HRID 1269832 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH:6]([O:10][C:11]2[C:12]([CH3:20])=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][N:15]=[CH:14]3)[CH2:5]1)(=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[OH-].[Na+]>O>[CH2:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH:6]([O:10][C:11]2[C:12]([CH3:20])=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][N:15]=[CH:14]3)[CH2:5]1)[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 18447172HCID 18447172, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18447189HCID 18447189, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of the 5-[(1-acetylpiperidin-3-yl)oxy]-4-methyl-1H-indazole (55.1 mg, 0.202 mmol) obtained in Example 455, lithium aluminum hydride (40 mg, 1.1 mmol) and tetrahydrofuran (2 ml) was stirred at 80° C. for 2.5 hours. The reaction mixture was ice-cooled, followed by adding thereto water (0.04 ml), a 2N-aqueous sodium hydroxide solution (0.08 ml) and water (0.12 ml) in that order. The precipitate was removed by filtration and the solvent was distilled off. Thereafter, the residue oil was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate/triethylamine=5/15/1) to obtain 5-[(1-ethylpiperidin-3-yl)oxy]-4-methyl-1H-indazole (14 mg, 28%).

Workup

  1. temperaturecooled
  2. additionby adding
  3. customThe precipitate was removed by filtration
  4. distillationthe solvent was distilled off
  5. customThereafter, the residue oil was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate/triethylamine=5/15/1)

Sources & evidence

ORD record
ord-e52fb042eb8d49fab95a332c420ccf72
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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