Potassium → 5-[4-[[3-Methyl-4-oxo-3,4-dihydroquinazolin-2-yl]methoxy]benzyl]thiazolidine-2,4-dione potassium salt

HRID 388416Notes

Reaction equation

HRID 388416 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[C:3]1[CH2:13][O:14][C:15]1[CH:28]=[CH:27][C:18]([CH2:19][CH:20]2[S:24][C:23](=[O:25])[NH:22][C:21]2=[O:26])=[CH:17][CH:16]=1.[K:29]>C1(C)C(C)=CC=CC=1.CO>[K:29].[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[C:3]1[CH2:13][O:14][C:15]1[CH:28]=[CH:27][C:18]([CH2:19][CH:20]2[S:24][C:23](=[O:25])[NH:22][C:21]2=[O:26])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 5462222PotassiumHCID 9889200Balaglitazone

Product 1

HCID 98891995-[4-[[3-Methyl-4-oxo-3,4-dihydroquinazolin-2-yl]methoxy]benzyl]thiazolidine-2,4-dione potassium saltYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 7237O-XyleneSolvent

Procedure

5-[4-[[3-Methyl-4-oxo-3,4-dihydroquinazolin-2-yl]methoxy]benzyl]thiazolidine-2,4-dione (40 g) was dissolved in a mixture of xylene (280 ml) and methanol (280 ml) at reflux temperature to get clear solution. Potassium tertariry butoxide (12.52 g) dissolved in methanol was added slowly drop wise. After complete addition, the reaction mass was stirred at room temperature for 1 hour. The precipitated compound was filtered, washed with methanol and dried the compound in oven at 60-80° C. to yield polymorphic Form 1 of 5-[4-[[3-methyl-4-oxo-3,4-dihydroquinazolin-2-yl]methoxy]benzyl]thiazolidine-2,4-dione potassium salt (40 g).

Workup

  1. temperatureat reflux temperature
  2. customto get clear solution
  3. additionwas added slowly drop wise
  4. additionAfter complete addition
  5. filtrationThe precipitated compound was filtered
  6. washwashed with methanol
  7. customdried the compound in oven at 60-80° C.

Sources & evidence

ORD record
ord-a6e065b5148d4b4f917a929a03892c51
Source dataset
uspto-grants-2013_02
Patent number
US08377950B2

Reaction notes

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