Sodium Hydroxide → HCID 23156137, compound

HRID 1890651Notes

Reaction equation

HRID 1890651 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:23]3[C:27]4=[N:28][C:29]([CH3:33])=[CH:30][C:31]([CH3:32])=[C:26]4[N:25]=[C:24]3[CH3:34])=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(OCC)(=O)C.Cl.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH3:34][C:24]1[N:23]([CH2:22][C:19]2[CH:20]=[CH:21][C:16]([NH:15][CH2:14][CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:17][CH:18]=2)[C:27]2=[N:28][C:29]([CH3:33])=[CH:30][C:31]([CH3:32])=[C:26]2[N:25]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21866389Hydrogen chloride-ethyl acetateHCID 694347614-[4-(2,5,7-trimethyl-3H-imidazo[4,5-b]pyridin-3-ylmethyl)phenylamino]methylpiperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 23156137HCID 23156137, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4-[4-(2,5,7-trimethyl-3H-imidazo[4,5-b]pyridin-3-ylmethyl)phenylamino]methylpiperidine-1-carboxylic acid tert-butyl ester (1.53 g, 3.31 mmol) obtained in Step 1 in chloroform (15 mL) was added with a 4 mol/L hydrogen chloride-ethyl acetate solution (7.0 mL) followed by stirring at room temperature for 2 hours. The reaction mixture was added with a 2 mol/L aqueous sodium hydroxide solution to control the pH to 12, and extracted with chloroform three times. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain Compound 157 (1.20 g, 3.3 mmol, 99%).

Workup

  1. extractionextracted with chloroform three times
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-860f8774b38e441f8d38e18cf71ce779
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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