Hydrochloric Acid → 4-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid

HRID 1851569Notes

Reaction equation

HRID 1851569 reaction equation
COC[N:4]1[C:12]2[C:7](=[C:8]([CH3:23])[CH:9]=[CH:10][C:11]=2[N:13]([CH3:22])[S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:16])=[O:15])[CH:6]=[C:5]1[C:24]([O:26]CC)=[O:25].Cl.O1CCCC1>C(O)C>[CH3:23][C:8]1[CH:9]=[CH:10][C:11]([N:13]([CH3:22])[S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:15])=[O:16])=[C:12]2[C:7]=1[CH:6]=[C:5]([C:24]([OH:26])=[O:25])[NH:4]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 57476005ethyl 1-(methoxymethyl)-4-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate

Product 1

HCID 574760074-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acidYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixed solution of ethyl 1-(methoxymethyl)-4-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate (4.0 g), 6N hydrochloric acid (20 mL), tetrahydrofuran (20 mL) and ethanol (60 mL) was stirred at 80° C. for 4 hr. The reaction solution was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained solid was dissolved in a mixed solution of tetrahydrofuran (40 mL) and methanol (40 mL), aqueous solution (20 mL) of 85% potassium hydroxide (2.2 g) was added, and the mixture was stirred at room temperature for 18 hr. The reaction solution was concentrated under reduced pressure, and the obtained residue was acidified with aqueous citric acid solution. The precipitated crystals were collected by filtration, thoroughly washed with water, and dried to give the title compound (3.3 g, yield 99%) as colorless crystals. MS:351 (MH+). melting point 223-225° C.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionThe obtained residue was diluted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe obtained solid was dissolved in a mixed solution of tetrahydrofuran (40 mL) and methanol (40 mL), aqueous solution (20 mL) of 85% potassium hydroxide (2.2 g)
  7. additionwas added
  8. concentrationThe reaction solution was concentrated under reduced pressure
  9. filtrationThe precipitated crystals were collected by filtration
  10. washthoroughly washed with water
  11. customdried

Sources & evidence

ORD record
ord-3e63bb951c65467c980fa6acbc42fc5e
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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