Lithium Hydroxide → 6-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethyl-1-benzothiophene-2-carboxylic acid

HRID 43801Notes

Reaction equation

HRID 43801 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C:12]2[CH:27]=[CH:26][C:15]3[C:16]([CH2:24][CH3:25])=[C:17]([C:19]([O:21]CC)=[O:20])[S:18][C:14]=3[CH:13]=2)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].[OH-].[Li+]>CO.C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C:12]2[CH:27]=[CH:26][C:15]3[C:16]([CH2:24][CH3:25])=[C:17]([C:19]([OH:21])=[O:20])[S:18][C:14]=3[CH:13]=2)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67548450HCID 67548450, compound

Product 1

HCID 601359066-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethyl-1-benzothiophene-2-carboxylic acidYield 87.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 6-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethyl-1-benzothiophene-2-carboxylate obtained in Example (183f) (49 mg) was dissolved in methanol (2 ml) and THF (2 ml). A 2 N aqueous lithium hydroxide solution (2 ml) was added, and the mixture was stirred at 50° C. for 30 minutes. The organic solvent was evaporated under reduced pressure, followed by neutralization with 1 N hydrochloric acid. The resulting solid was collected by filtration, washed with distilled water and ethyl acetate, and dried under reduced pressure at 45° C. to obtain 40 mg of the title compound as a solid.

Workup

  1. customThe organic solvent was evaporated under reduced pressure
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with distilled water and ethyl acetate
  4. customdried under reduced pressure at 45° C.

Sources & evidence

ORD record
ord-4cf3fdfb0aed4006b41833687625bf32
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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