Tetrahydrofuran → 1-(4-Fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxylic acid

HRID 2368475Notes

Reaction equation

HRID 2368475 reaction equation
CN1C=C(CN(C)C(C2N(C3C=CC(F)=CC=3)C(S)=NC=2)=O)C(C)=N1.[F:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:37]([C:38]([O:40]CC)=[O:39])=[CH:36][N:35]=[C:34]2[S:43][CH2:44][C:45]2[C:50]([F:51])=[CH:49][CH:48]=[C:47]([F:52])[C:46]=2[F:53])=[CH:29][CH:28]=1.O.[OH-].[Li+].C1COCC1>O.CO>[F:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:37]([C:38]([OH:40])=[O:39])=[CH:36][N:35]=[C:34]2[S:43][CH2:44][C:45]2[C:50]([F:51])=[CH:49][CH:48]=[C:47]([F:52])[C:46]=2[F:53])=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 71117421Ethyl 1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxylateHCID 178434002N-((1,3-dimethyl-1H-pyrazol-4-yl)methyl)-1-(4-fluorophenyl)-2-mercapto-N-methyl-1H-imidazole-5-carboxamide

Product 1

HCID 711173271-(4-Fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-(4-Fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxylic acid (11) was prepared in a similar manner as that described for the synthesis of compound 7 using ethyl 1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxylate (10) (284 mg, 0.69 mmol), lithium hydroxide monohydrate (66 mg, 2.76 mmol), THF (0.2 mL), methanol (0.4 mL), and water (0.8 mL).

Sources & evidence

ORD record
ord-c2cf030db24b4c6cbaf0f6f3f40d80cc
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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