Sodium Hydroxide → HCID 23156199, compound

HRID 1890653Notes

Reaction equation

HRID 1890653 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:11][C:12]1[N:22]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31]([CH:33]3[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]3)=O)=[CH:26][CH:25]=2)[C:15]2=[N:16][C:17]([CH3:21])=[CH:18][C:19]([CH3:20])=[C:14]2[N:13]=1.[OH-].[Na+]>C1COCC1>[CH3:11][C:12]1[N:22]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([NH:30][CH2:31][CH:33]3[CH2:34][CH2:35][N:36]([CH3:39])[CH2:37][CH2:38]3)=[CH:26][CH:25]=2)[C:15]2=[N:16][C:17]([CH3:21])=[CH:18][C:19]([CH3:20])=[C:14]2[N:13]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 86615035HCID 86615035, compound

Product 1

HCID 23156199HCID 23156199, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Under argon atmosphere, a solution of aluminum trichloride (0.136 g, 1.02 mmol) in THF (2.5 mL) was dropped into a solution of lithium aluminum hydride (77.4 mg, 2.04 mmol) in THF (3.0 mL) at 0° C. Then, a solution of 1-methylpiperidine-4-carboxylic acid [4-(2,5,7-trimethyl-3H-imidazo[4,5-b]pyridin-3-ylmethyl)phenyl amide] (1.53 g, 3.31 mmol) obtained in Step 1 in THF (3.0 mL) was dropped into the mixture. The mixture was stirred at 0° C. for 15 minutes, then at room temperature for 1.5 hours. The reaction mixture was added with a 2 mol/L aqueous sodium hydroxide solution and extracted with ethyl acetate three times. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained crystals were recrystallized from ethanol-diisopropyl ether to obtain Compound 159 (44.3 mg, 0.12 mmol, 23%).

Workup

  1. waitat room temperature for 1.5 hours
  2. extractionextracted with ethyl acetate three times
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained crystals were recrystallized from ethanol-diisopropyl ether

Sources & evidence

ORD record
ord-dede09a1d5be41f2963c89477b019d3b
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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