Sodium Hydroxide → 3-[5-(2-aminopyridin-4-yl)-4-(4-fluorophenyl)-1-methyl-1H-imidazol-2-ylsulfanyl]propionic acid

HRID 2117741Notes

Reaction equation

HRID 2117741 reaction equation
C([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[N:15]([CH3:16])[C:14]([S:17][CH2:18][CH2:19][C:20]([O:22]CC)=[O:21])=[N:13][C:12]=2[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH:8]=[CH:7][N:6]=1)(=O)C.[OH-].[Na+]>Cl>[NH2:4][C:5]1[CH:10]=[C:9]([C:11]2[N:15]([CH3:16])[C:14]([S:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[N:13][C:12]=2[C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)[CH:8]=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58752321Ethyl 3-[5-(2-acetylaminopyridin-4-yl)-4-(4-fluorophenyl)-1-methyl-1H-imidazol-2-ylsulfanyl]propionate

Product 1

HCID 587523233-[5-(2-aminopyridin-4-yl)-4-(4-fluorophenyl)-1-methyl-1H-imidazol-2-ylsulfanyl]propionic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

50 ml of HCl 10% are added to ethyl 3-[5-(2-acetylaminopyridin-4-yl)-4-(4-fluorophenyl)-1-methyl-1H-imidazol-2-ylsulfanyl]propionate (0.67 mmol/0.297 g), and the mixture is stirred at room temperature for 6 h. The mixture is then slowly neutralized using 2N NaOH, resulting in the precipitation of 3-[5-(2-aminopyridin-4-yl)-4-(4-fluorophenyl)-1-methyl-1H-imidazol-2-ylsulfanyl]propionic acid as a whitish powder. The precipitate is filtered off with suction, washed with a little ice-cold water and dried over P2O5.

Sources & evidence

ORD record
ord-1a1418da5ccf43ae80de135b8a3f8c8d
Source dataset
uspto-grants-2008_10
Patent number
US07442713B2

Reaction notes

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