Ethanol → HCID 86760993, compound

HRID 1437165Notes

Reaction equation

HRID 1437165 reaction equation
COC(=O)C1C=CC=C(CN2[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][CH2:29][CH3:30])[CH:18]=3)CC2)C=1.[OH-:32].[Na+].[CH2:34]([OH:36])[CH3:35]>>[CH2:29]([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]([C:15]2[CH:16]=[CH:17][CH:14]=[CH:15][C:35]=2[C:34]([OH:32])=[O:36])[N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:20]2)=[CH:18]1)[CH3:30]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 68894362HCID 68894362, compound

Product 1

HCID 86760993HCID 86760993, compound

Procedure

0.58 g (1.28 mmol) of 3-{4-[1-(2-ethoxyethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-piperidin-1-ylmethyl}-benzoic acid methyl ester were dissolved in 5 ml of ethyl alcohol and 1.93 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 dichloromethane. The organic phase was washed with water and brine, dried with magnesium sulphate, filtrated and evaporated. The crude material weighed 0.65 g and was purified by flash chromatography over silica gel affording 0.3 g (54% 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 dichloromethane
  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 0.3 g (54% of yield) of the expected product

Sources & evidence

ORD record
ord-26d0ada436c24f97bd6207f040f22195
Source dataset
uspto-grants-2009_11
Patent number
US07622480B2

Reaction notes

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