Hydride → HCID 178462535, compound

HRID 862195Notes

Reaction equation

HRID 862195 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([CH:13]3[CH2:18][CH2:17][N:16]([C:19](=O)[CH3:20])[CH2:15][CH2:14]3)=[N:10][C:9]=2[C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.[Li].[H-]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([CH:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH3:20])[CH2:15][CH2:14]3)=[N:10][C:9]=2[C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 166653HydrideHCID 3028194LithiumHCID 178473784HCID 178473784, compound

Product 1

HCID 178462535HCID 178462535, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring suspension of 4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1H-imidazol-2-yl]-1-acetylpiperidine (0.11 mmol,41.4 mg) in THF (1.0 mL) was added lithium alumininum hydride (0.14 mmol, 0.14 mL of a 1M solution in THF) and the reaction stirred at room temperature for 2 h. The reaction was then quenched with water (0.1 mL), diluted with ethyl acetate (25 mL), the suspension filtered, the filtrates dried over anhydrous sodium sulfate and the solvent evaporated under reduced pressure. The residue was triturated with diethyl ether to give 25 mg of the title compound as a white powder. mp=242°-244° C.

Workup

  1. customThe reaction was then quenched with water (0.1 mL)
  2. additiondiluted with ethyl acetate (25 mL)
  3. filtrationthe suspension filtered
  4. dry with materialthe filtrates dried over anhydrous sodium sulfate
  5. customthe solvent evaporated under reduced pressure
  6. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-fbb10a97211747cfb9e9d894e5551bfe
Source dataset
uspto-grants-1998_02
Patent number
US05717100

Reaction notes

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