Aluminium lithium hydride → HCID 178457505, compound

HRID 1269965Notes

Reaction equation

HRID 1269965 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[C:16]([O:17][C@@H:18]2[CH2:23][CH2:22][C@H:21]([NH:24][C:25](=O)[CH2:26][CH3:27])[CH2:20][CH2:19]2)=[CH:15][C:14]([CH3:29])=[C:13]2[C:9]=1[CH:10]=[N:11][NH:12]2>O1CCCC1>[CH3:7][C:8]1[C:16]([O:17][C@@H:18]2[CH2:23][CH2:22][C@H:21]([NH:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:19]2)=[CH:15][C:14]([CH3:29])=[C:13]2[C:9]=1[CH:10]=[N:11][NH:12]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178460281HCID 178460281, compound

Product 1

HCID 178457505HCID 178457505, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (70 mg, 1.84 mmol) was added to a tetrahydrofuran solution (5 ml) of the cis-N-{4-[(4,7-dimethyl-1H-indazol-5-yl)oxy]cyclohexyl}propanamide (116 mg, 0.368 mmol) obtained in Example 668, and the resulting mixture was heated under reflux for 5 hours. After the reaction solution was diluted with 10 ml of tetrahydrofuran, the reaction was terminated by careful addition of water (76 μl), a 4N-aqueous sodium hydroxide solution (76 μl) and water (230 μl) in that order under ice-cooling. The reaction solution thus treated was filtered by the use of Celite and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by a preparative thin-layer silica gel chromatography (chloroform/methanol/aqueous ammonia=7:1:0.1) to obtain cis-N-{4-[(4,7-dimethyl-1H-indazol-5-yl)oxy]cyclohexyl}-N-propylamine (64 mg, 58%).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customthe reaction was terminated by careful addition of water (76 μl)
  4. temperaturea 4N-aqueous sodium hydroxide solution (76 μl) and water (230 μl) in that order under ice-cooling
  5. additionThe reaction solution thus treated
  6. filtrationwas filtered by the use of Celite
  7. distillationthe solvent was distilled off under reduced pressure
  8. customto obtain a crude product
  9. customThe crude product was purified by a preparative thin-layer silica gel chromatography (chloroform/methanol/aqueous ammonia=7:1:0.1)

Sources & evidence

ORD record
ord-ac0402733fdc4c90beb14cd8ecb6d986
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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