Lithium Hydroxide → 1-(4-Fluorophenyl)-2-((2,3,6-trifluorobenzyl)sulfonyl)-1H-imidazole-5-carboxylic acid

HRID 2368484Notes

Reaction equation

HRID 2368484 reaction equation
CN1C=C(CN(C)C(C2N(C3C=CC(F)=CC=3)C(S)=NC=2)=[O:10])C(C)=N1.[F:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:37]([C:38](N(OC)C)=[O:39])=[CH:36][N:35]=[C:34]2[S:44]([CH2:47][C:48]2[C:53]([F:54])=[CH:52][CH:51]=[C:50]([F:55])[C:49]=2[F:56])(=[O:46])=[O:45])=[CH:29][CH:28]=1.[OH-].[Li+].C1COCC1>O.CO>[F:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:37]([C:38]([OH:10])=[O:39])=[CH:36][N:35]=[C:34]2[S:44]([CH2:47][C:48]2[C:53]([F:54])=[CH:52][CH:51]=[C:50]([F:55])[C:49]=2[F:56])(=[O:45])=[O:46])=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 866775471-(4-fluorophenyl)-N-methoxy-N-methyl-2-((2,3,6-trifluorobenzyl)sulfonyl)-1H-imidazole-5-carboxamideHCID 178434002N-((1,3-dimethyl-1H-pyrazol-4-yl)methyl)-1-(4-fluorophenyl)-2-mercapto-N-methyl-1H-imidazole-5-carboxamide

Product 1

HCID 711187801-(4-Fluorophenyl)-2-((2,3,6-trifluorobenzyl)sulfonyl)-1H-imidazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-(4-Fluorophenyl)-2-((2,3,6-trifluorobenzyl)sulfonyl)-1H-imidazole-5-carboxylic acid (22) was prepared in a similar manner as that described for the synthesis of compound 7 using 1-(4-fluorophenyl)-N-methoxy-N-methyl-2-((2,3,6-trifluorobenzyl)sulfonyl)-1H-imidazole-5-carboxamide (21) (50 mg, 0.11 mmol), lithium hydroxide (10 mg, 0.44 mmol), THF (0.1 mL), methanol (0.2 mL), and water (0.4 mL).

Sources & evidence

ORD record
ord-005e373067b2475fa44234e6ca50cf31
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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