Sodium Hydroxide → HCID 23156197, compound

HRID 1890657Notes

Reaction equation

HRID 1890657 reaction equation
[CH2:1]([C:3]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][CH2:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[CH:16][CH:15]=2)[C:6]2=[N:7][CH:8]=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].[CH3:28][N:29]1[CH2:34][CH2:33][C:32](=O)[CH2:31][CH2:30]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl>[CH2:1]([C:3]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][CH2:21][CH:22]3[CH2:23][CH2:24][N:25]([CH:32]4[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]4)[CH2:26][CH2:27]3)=[CH:16][CH:15]=2)[C:6]2=[N:7][CH:8]=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 740491-Methyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydrideHCID 23156140HCID 23156140, compound

Product 1

HCID 23156197HCID 23156197, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of Compound 165 (0.250 g, 0.69 mmol) in 1,2-dichloroethane (3.5 mL) was added with 1-methyl-4-piperidone (0.128 mL, 1.04 mmol) followed by stirring for 20 minutes. The mixture was added with sodium triacetoxyborohydride (0.439 g, 2.07 mmol) followed by stirring at room temperature for 4 hours. The reaction mixture was added with a 2 mol/L aqueous sodium hydroxide solution, and extracted with dichloromethane three times. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:2 mol/L ammonia-methanol solution=19:1). The obtained crystals were recrystallized from ethanol-diisopropyl ether to obtain Compound 166 (0.172 g, 0.37 mmol, 54%).

Workup

  1. stirringby stirring at room temperature for 4 hours
  2. extractionextracted with dichloromethane three times
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform:2 mol/L ammonia-methanol solution=19:1)
  6. customThe obtained crystals were recrystallized from ethanol-diisopropyl ether

Sources & evidence

ORD record
ord-386f841545b940ea9a8ea859e3ebf25e
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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