Sodium Hydroxide → HCID 10287414, compound

HRID 1437158Notes

Reaction equation

HRID 1437158 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[C:25]4[C:20](=[N:21][CH:22]=[CH:23][CH:24]=4)[N:19]([CH2:26][CH2:27][O:28][CH3:29])[CH:18]=3)[CH2:13][CH2:12]2)[CH:5]=1.[OH-].[Na+]>C(O)C>[CH3:29][O:28][CH2:27][CH2:26][N:19]1[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:25]2[C:17]([CH:14]2[CH2:15][CH2:16][N:11]([CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:30])=[O:2])[CH2:12][CH2:13]2)=[CH:18]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68896791HCID 68896791, compound

Product 1

HCID 10287414HCID 10287414, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.66 g (1.62 mmol) of 3-{4-[1-(2-methoxyethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-piperidin-1-ylmethyl}-benzoic acid methyl ester were dissolved in 0.8 ml of ethyl alcohol and 2.43 ml of 2 N sodium hydroxide were added. After stirring at room temperature for 20 hours, the solvent was evaporated under reduced pressure and the residue dissolved in water. The mixture was neutralised with 2 N hydrochloric acid and extracted twice with dichlormethane. The organic phase was washed with water and brine, dried with magnesium sulphate, filtrated and evaporated. The crude material weighed 0.46 g and was purified by flash chromatography over silica gel affording 0.2 g (31% of yield) of the expected product.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionthe residue dissolved in water
  3. extractionextracted twice with dichlormethane
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried with magnesium sulphate
  6. filtrationfiltrated
  7. customevaporated
  8. customwas purified by flash chromatography over silica gel affording 0.2 g (31% of yield) of the expected product

Sources & evidence

ORD record
ord-d1a1a27850b541a9a5fd2fc3ac0b2927
Source dataset
uspto-grants-2009_11
Patent number
US07622480B2

Reaction notes

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