Methanol → [2-(7-Methyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetic acid

HRID 1042199Notes

Reaction equation

HRID 1042199 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][CH:6]1[S:10][C:9]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([O:20][C:21]2[CH:22]=[N:23][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][CH:26]=2)=[CH:15][C:14]=3[CH3:31])=[N:8][CH2:7]1)C.CO.[OH-].[K+]>O1CCCC1>[CH3:31][C:14]1[CH:15]=[C:16]([O:20][C:21]2[CH:22]=[N:23][C:24]([S:27]([CH3:30])(=[O:28])=[O:29])=[CH:25][CH:26]=2)[CH:17]=[C:18]2[C:13]=1[NH:12][C:11]([C:9]1[S:10][CH:6]([CH2:5][C:4]([OH:32])=[O:3])[CH2:7][N:8]=1)=[CH:19]2

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 58081030HCID 58081030, compound

Product 1

HCID 58081062[2-(7-Methyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetic acidYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl[2-(7-methyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetate (2.59 g), methanol (25 mL), and tetrahydrofuran (25 mL) was added an aqueous solution (15 mL) of potassium hydroxide (1.0 g), and the mixture was stirred at room temperature for 6 hr. The reaction solution was concentrated, acidified with aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained pale-yellow crystals were washed with ethyl acetate-hexane to give the title compound (2.33 g, yield 96%) as pale-yellow crystals.

Workup

  1. concentrationThe reaction solution was concentrated
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. washThe obtained pale-yellow crystals were washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-6d9b7162980c4407b59308f9d68b311c
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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