Sodium Hydroxide → cis(+/-)-2-(4-{[(5-Ethyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methyl-1,3-thiazole-4-carboxylic acid

HRID 43482Notes

Reaction equation

HRID 43482 reaction equation
[CH2:1]([C:3]1[NH:7][C:6]([C:8]([NH:10][C@H:11]2[CH2:16][CH2:15][N:14]([C:17]3[S:18][C:19]([CH3:27])=[C:20]([C:22]([O:24]CC)=[O:23])[N:21]=3)[CH2:13][C@H:12]2[O:28][CH3:29])=[O:9])=[N:5][C:4]=1[C:30]([F:33])([F:32])[F:31])[CH3:2].[OH-].[Na+]>CO>[CH2:1]([C:3]1[NH:7][C:6]([C:8]([NH:10][C@H:11]2[CH2:16][CH2:15][N:14]([C:17]3[S:18][C:19]([CH3:27])=[C:20]([C:22]([OH:24])=[O:23])[N:21]=3)[CH2:13][C@H:12]2[O:28][CH3:29])=[O:9])=[N:5][C:4]=1[C:30]([F:33])([F:31])[F:32])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86648493Ethyl cis(+/-)-2-(4-{[(5-ethyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methyl-1,3-thiazole-4-carboxylate

Product 1

HCID 86648494cis(+/-)-2-(4-{[(5-Ethyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methyl-1,3-thiazole-4-carboxylic acidYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl cis(±)-2-(4-{[(5-ethyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methyl-1,3-thiazole-4-carboxylate obtained in Example (40f) (29.2 mg, 0.060 mmol) was dissolved in methanol (1 mL). The solution was subjected to the same operation as in Example (36g) using a 1 N aqueous sodium hydroxide solution (1.5 mL), to obtain 24.0 mg of the title compound as a white solid (87%).

Sources & evidence

ORD record
ord-5b0eea087a06417ba2eca281b17aa4ba
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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