Sodium Hydroxide → HCID 68614796, compound

HRID 643701Notes

Reaction equation

HRID 643701 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:13][C:14](=O)[CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:5]([NH:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)=[N:6][CH:7]=1.[OH-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[N:13]=[C:14]([CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[N:8]([CH2:9][CH:10]3[CH2:12][CH2:11]3)[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68615377HCID 68615377, compound

Product 1

HCID 68614796HCID 68614796, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-{5-bromo-2-[(cyclopropylmethyl)amino]pyridin-3-yl}-3,3-dimethylbutanamide (5.04 g, 14.8 mmol, step E) and 2 N sodium hydroxide solution (10 mL) in ethanol (90 mL) was stirred under reflux for 21 h. After concentration, the residue was dissolved in water (50 mL) and the mixture was extracted with ethyl acetate (30 mL×2). The organic extracts were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1 as eluent) to give the title compound (3.9 g, 82%) as a pale pink solid.

Workup

  1. temperatureunder reflux for 21 h
  2. concentrationAfter concentration
  3. dissolutionthe residue was dissolved in water (50 mL)
  4. extractionthe mixture was extracted with ethyl acetate (30 mL×2)
  5. dry with materialThe organic extracts were dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1 as eluent)

Sources & evidence

ORD record
ord-6de132ae4f184db3a90ee943e9caff6e
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

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