Sodium Hydroxide → HCID 59398277, compound

HRID 2193151Notes

Reaction equation

HRID 2193151 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH:12][CH:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][N:21]4[C:30]5[C:25](=[C:26](/[CH:33]=[CH:34]/[C:35]([O:37]CC)=[O:36])[CH:27]=[C:28]([O:31][CH3:32])[CH:29]=5)[CH:24]=[CH:23][C:22]4=[O:40])[CH2:15][CH2:14]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH:12][CH:13]3[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][N:21]4[C:30]5[C:25](=[C:26](/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36])[CH:27]=[C:28]([O:31][CH3:32])[CH:29]=5)[CH:24]=[CH:23][C:22]4=[O:40])[CH2:17][CH2:18]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86643185ethyl (2E)-3-(1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-5-yl)acrylate

Product 1

HCID 59398277HCID 59398277, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2 mL of an ethanol solution containing 0.10 g of ethyl (2E)-3-(1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-5-yl)acrylate, 0.22 mL of 20% aqueous sodium hydroxide solution was added and stirred at room temperature for 3 hours. Ethanol was removed under reduced pressure, water was added, and adjusted to pH 6.0 with 1 mol/L hydrochloric acid under ice-cooling. The resulting solid was filtered to afford 85 mg of (2E)-3-(1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-5-yl)acrylic acid as a light brown solid.

Workup

  1. additionwas added
  2. customEthanol was removed under reduced pressure, water
  3. additionwas added
  4. temperaturecooling
  5. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-d76e916667334ed4941f629c77398ec0
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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