Methanol → HCID 59615408, compound

HRID 43563Notes

Reaction equation

HRID 43563 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[CH2:17][N:16]([C:21]2[S:22][C:23]([C:26]([O:28]CC)=[O:27])=[CH:24][N:25]=2)[CH2:15]3)=[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:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[CH2:17][N:16]([C:21]2[S:22][C:23]([C:26]([OH:28])=[O:27])=[CH:24][N:25]=2)[CH2:15]3)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 67548627ethyl 2-(5-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-1,3-dihydro-2H-isoindol-2-yl)-1,3-thiazole-5-carboxylate

Product 1

HCID 59615408HCID 59615408, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The same operation as in Example (90g) was performed using ethyl 2-(5-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-1,3-dihydro-2H-isoindol-2-yl)-1,3-thiazole-5-carboxylate obtained in Example (92b) (92 mg, 0.21 mmol), 2 N lithium hydroxide (3 mL, 6 mmol), methanol (5 mL) and dichloromethane (5 mL). Purification by reverse phase chromatography (elution solvent: acetonitrile/water=0/1, 1/1, 4/1) gave 49 mg of the title compound as a light brown solid (57%).

Workup

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

Sources & evidence

ORD record
ord-1fd7453214454d7c84551cb7db6d3ff4
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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