Hydrochloric Acid → cis(+/-)-2-(4-{[(5-Methyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-thiazole-5-carboxylic acid
Reaction equation
[CH3:1][C:2]1[NH:6][C:5]([C:7]([NH:9][C@H:10]2[CH2:15][CH2:14][N:13]([C:16]3[S:17][C:18]([C:21]([O:23]CC)=[O:22])=[CH:19][N:20]=3)[CH2:12][C@H:11]2[O:26][CH3:27])=[O:8])=[N:4][C:3]=1[C:28]([F:31])([F:30])[F:29].[OH-].[Na+].Cl>CO>[CH3:1][C:2]1[NH:6][C:5]([C:7]([NH:9][C@H:10]2[CH2:15][CH2:14][N:13]([C:16]3[S:17][C:18]([C:21]([OH:23])=[O:22])=[CH:19][N:20]=3)[CH2:12][C@H:11]2[O:26][CH3:27])=[O:8])=[N:4][C:3]=1[C:28]([F:31])([F:29])[F:30]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethyl cis(±)-2-(4-{[(5-methyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-thiazole-5-carboxylate obtained in Example (36f) (30 mg, 0.065 mmol) was dissolved in methanol (1 mL). A 1 N aqueous sodium hydroxide solution (1 mL) was added, and the mixture was stirred at room temperature for 1.5 hours. The reaction solution was neutralized with 1 N hydrochloric acid, and the residue was purified by reverse phase silica gel column chromatography (elution solvent: distilled water, methanol/distilled water=20/80, 60/40) to obtain 9.1 mg of the title compound as a white solid (32%).
Workup
- distillationthe residue was purified by reverse phase silica gel column chromatography (elution solvent: distilled water, methanol/distilled water=20/80, 60/40)
Sources & evidence
- ORD record
- ord-cbf8e36f72864cf8ace420cc75401e2f
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536197B2
Reaction notes
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