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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

HRID 43471
Notes
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Reaction equation

HRID 43471 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86648484Ethyl cis(+/-)-2-(4-{[(5-methyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-thiazole-5-carboxylate

Product 1

HCID 86648483cis(+/-)-2-(4-{[(5-Methyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-thiazole-5-carboxylic acidYield 32.3%

Reagents, catalysts & solvents

1
HCID 887MethanolSolvent

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

  1. 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536197B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes