Lithium Hydroxide → 1-(4-Fluorophenyl)-2-((pyridin-4-ylmethyl)thio)-1H-imidazole-5-carboxylic acid

HRID 2368510Notes

Reaction equation

HRID 2368510 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=[C:9]2[S:16][CH2:17][C:18]2[C:23](F)=[CH:22]C=[C:20](F)[C:19]=2F)=[CH:4][CH:3]=1.[NH:27]1C(C([O-])=O)=CN=C1.[Li+].[OH-]>C1COCC1.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=[C:9]2[S:16][CH2:17][C:18]2[CH:19]=[CH:20][N:27]=[CH:22][CH:23]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 69999361H-imidazole-5-carboxylateHCID 711173271-(4-Fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxylic acid

Product 1

HCID 711176951-(4-Fluorophenyl)-2-((pyridin-4-ylmethyl)thio)-1H-imidazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Fluorophenyl)-2-((pyridin-4-ylmethyl)thio)-1H-imidazole-5-carboxylic acid (51) was prepared in a similar manner as that described for the synthesis of compound 11 using ethyl 1-(4-fluorophenyl)-2-(pyridine-4-ylmethyl)thio)-1H-imidazole-5-carboxylate (50) (390 mg, 1.09 mmol), 1N LiOH (5 mL) in THF (5 mL) and MeOH (5 mL).

Sources & evidence

ORD record
ord-dc5b6569e2724ae2b843aff680ad212c
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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