Lithium hydroxide, monohydrate → HCID 67189619, compound

HRID 551819Notes

Reaction equation

HRID 551819 reaction equation
[NH:1]1[CH:5]=[C:4]([CH:6]2[CH2:10][CH2:9][N:8]([C:11]([N:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]([C:23]4[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=4)[CH2:15][CH2:14]3)=[O:12])[CH2:7]2)[CH:3]=[N:2]1.O.[OH-].[Li+]>O1CCCC1.CO.O>[NH:1]1[CH:5]=[C:4]([CH:6]2[CH2:10][CH2:9][N:8]([C:11]([N:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]([C:23]4[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:31][CH:32]=4)[CH2:15][CH2:14]3)=[O:12])[CH2:7]2)[CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67188173HCID 67188173, compound

Product 1

HCID 67189619HCID 67189619, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

4.2 g of methyl 4-[4-{[3-(1H-pyrazol-4-yl)pyrrolidin-1-yl]carbonyl}-3,4-dihydroquinoxalin-1(2H)-yl]benzoate and 50 ml of a tetrahydrofuran/methanol/water 2/1/1 mixture are introduced into a 250 ml round-bottomed flask equipped with a magnetic stirrer and placed in an ice bath. 1.63 g of lithium hydroxide monohydrate are added and the reaction mixture is stirred at ambient temperature for 18 h. After evaporating the organic solvents, citric acid is added up to pH 5. The precipitate is filtered off and dried under vacuum. 3.87 g of 4-[4-{[3-(1H-pyrazol-4-yl)pyrrolidin-1-yl]carbonyl}-3,4-dihydroquinoxalin-1(2H)-yl]benzoic acid are obtained.

Workup

  1. customequipped with a magnetic stirrer
  2. customplaced in an ice bath
  3. customAfter evaporating the organic solvents, citric acid
  4. additionis added up to pH 5
  5. filtrationThe precipitate is filtered off
  6. customdried under vacuum

Sources & evidence

ORD record
ord-60f476268b1444e8931e710c1c2513ad
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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