Lithium Hydroxide → HCID 59615401, compound

HRID 1425035Notes

Reaction equation

HRID 1425035 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[S:19][C:20]([C:23]([O:25]CC)=[O:24])=[CH:21][N:22]=3)=[CH:14][CH:13]=2)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].[OH-].[Li+]>CO.ClCCl>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[S:19][C:20]([C:23]([OH:25])=[O:24])=[CH:21][N:22]=3)=[CH:14][CH:13]=2)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67548532HCID 67548532, compound

Product 1

HCID 59615401HCID 59615401, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl 2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}phenyl)-1,3-thiazole-5-carboxylate obtained in Example (91c) (89 mg, 0.22 mmol) was dissolved in methanol (15 mL) and dichloromethane (10 mL). A 2 N aqueous lithium hydroxide solution (3 mL, 6 mmol) was added, and the mixture was stirred at 70° C. for 30 minutes. The organic solvent was evaporated under reduced pressure and 1 N hydrochloric acid was added until the pH of the solution was about 4. The resulting solid was collected by filtration and washed with distilled water to obtain 67 mg of the title compound as a light brown solid (80%).

Workup

  1. customThe organic solvent was evaporated under reduced pressure and 1 N hydrochloric acid
  2. additionwas added until the pH of the solution
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with distilled water

Sources & evidence

ORD record
ord-f0bdea777e0a4474a11b2e953a809750
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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