Potassium Hydroxide → 2-{4-Methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazole-4-carboxylic acid

HRID 1851573Notes

Reaction equation

HRID 1851573 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]([CH3:20])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:21]1[S:22][CH:23]=[C:24]([C:26]([O:28]CC)=[O:27])[N:25]=1)[NH:6]2.[OH-].[K+]>O1CCCC1.CO.C(OCC)(=O)C>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]([CH3:20])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:21]1[S:22][CH:23]=[C:24]([C:26]([OH:28])=[O:27])[N:25]=1)[NH:6]2

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 136060823Ethyl 2-{4-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazole-4-carboxylate

Product 1

HCID 1360608042-{4-Methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazole-4-carboxylic acidYield 98%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 2-{4-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazole-4-carboxylate (0.40 g) was dissolved in a mixed solution of tetrahydrofuran (15 mL) and methanol (15 mL), aqueous solution (5 mL) of 85% potassium hydroxide (0.20 g) was added, and the mixture was stirred at room temperature for 18 hr. The reaction solution was diluted with ethyl acetate, washed with aqueous citric acid solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (368 mg, yield 98%) as pale-yellow crystals. MS:434 (MH+).

Workup

  1. additionwas added
  2. washwashed with aqueous citric acid solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e0cdbe8b017490eb8d71bc59f63b987
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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