Methanol → HCID 59615437, compound

HRID 43567Notes

Reaction equation

HRID 43567 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:24]([O:26]CC)=[O:25])=[C:21]([CH3:23])[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:24]([OH:26])=[O:25])=[C:21]([CH3:23])[N:22]=3)=[CH:14][CH:13]=2)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 67548366Ethyl 2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}phenyl)-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 59615437HCID 59615437, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The same operation as in Example (90g) was performed using ethyl 2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}phenyl)-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (94c) (96 mg, 0.23 mmol), 2 N lithium hydroxide (2 mL, 4 mmol), methanol (5 mL) and dichloromethane (3 mL). Purification by reverse phase chromatography (elution solvent: THF/water=0/1, 1/1, 4/1) gave 69 mg of the title compound as a light brown solid (77%).

Workup

  1. customPurification
  2. washby reverse phase chromatography (elution solvent: THF/water=0/1, 1/1, 4/1)

Sources & evidence

ORD record
ord-f1c5bc0d210d45a180bc7ec4109fdab6
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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