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

HRID 2368522Notes

Reaction equation

HRID 2368522 reaction equation
F[C:2]1C=CC(N2C(C(O)=O)=CN=C2SCC2C(F)=CC=C(F)C=2F)=CC=1.[F:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]2[C:38]([C:39]([O-:41])=[O:40])=[CH:37][N:36]=[C:35]2[NH:42][CH2:43][C:44]2[C:49]([F:50])=[CH:48][CH:47]=[C:46]([F:51])[C:45]=2[F:52])=[CH:30][CH:29]=1>C1COCC1.CO>[CH3:2][C:37]1[N:36]=[C:35]([NH:42][CH2:43][C:44]2[C:49]([F:50])=[CH:48][CH:47]=[C:46]([F:51])[C:45]=2[F:52])[N:34]([C:31]2[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=2)[C:38]=1[C:39]([OH:41])=[O:40]

Participants

5

Reactant 2

HCID 711173271-(4-Fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxylic acidHCID 866775561-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)amino)-1H-imidazole-5-carboxylate

Product 1

HCID 71117800Methyl 1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)amino)-1H-imidazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)amino)-1H-imidazole-5-carboxylic acid (69) was prepared in a similar manner as that described for the synthesis of compound 11 using 1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)amino)-1H-imidazole-5-carboxylate (68) (60 mg, 0.158 mmol), 1NLiOH (5 mL) in THF (5 mL) and MeOH (5 mL).

Sources & evidence

ORD record
ord-c336bdd9932c49fd9c05a3b835f6ea10
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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