Lithium hydroxide, monohydrate → 4-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-imidazo[1,2-a]pyridin-2-ylsulfanyl]-butyric acid

HRID 215975Notes

Reaction equation

HRID 215975 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][S:7][C:8]1[N:9]=[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]2[C:16]=1[CH2:17][C:18]1[C:19]2[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:20]=2[S:21][CH:22]=1.O.[OH-].[Li+]>C1COCC1.O>[CH3:27][C:26]1[C:19]2[C:18]([CH2:17][C:16]3[N:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]4=[N:9][C:8]=3[S:7][CH2:6][CH2:5][CH2:4][C:3]([OH:28])=[O:2])=[CH:22][S:21][C:20]=2[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 591767234-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-imidazo[1,2-a]pyridin-2-ylsulfanyl]-butyric acid methyl ester

Product 1

HCID 591767254-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-imidazo[1,2-a]pyridin-2-ylsulfanyl]-butyric acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 100 mg (0.24 mmol) of 4-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-imidazo[1,2-a]pyridin-2-ylsulfanyl]-butyric acid methyl ester in 2 mL of THF is treated with a solution of 20 mg (0.48 mmol) of lithium hydroxide monohydrate in 1 mL of water at room temperature. The resulting mixture is heated to 40° C., and stirred at this temperature for 3 h. The reaction mixture is then cooled to room temperature and concentrated in vacuo. The residue is diluted with water and neutralized with 1N HCl solution. The product is extracted with ethyl acetate, and the organic layer is separated. The organic layer is washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography eluting with 3˜10% methanol in dichloromethane solution to give the title compound. LCMS (ESMS): m/z 397 (M+H+)

Workup

  1. temperatureThe reaction mixture is then cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additionThe residue is diluted with water and neutralized with 1N HCl solution
  4. extractionThe product is extracted with ethyl acetate
  5. customthe organic layer is separated
  6. washThe organic layer is washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue is purified by flash chromatography
  11. washeluting with 3˜10% methanol in dichloromethane solution

Sources & evidence

ORD record
ord-9f62dbfcc2b2459da38f560b52c55fbd
Source dataset
uspto-grants-2012_06
Patent number
US08193214B2

Reaction notes

Loading…