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

HRID 2368523Notes

Reaction equation

HRID 2368523 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]2SCC2C(F)=CC=C(F)C=2F)=[CH:4][CH:3]=1.CC1N([NH:36][CH2:37][C:38]2[C:43]([F:44])=[CH:42][CH:41]=[C:40]([F:45])[C:39]=2[F:46])C(C([O-])=O)=CN=1.[Li+].[OH-].[CH2:49]1COCC1>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[N:36]([CH3:49])[CH2:37][C:38]2[C:43]([F:44])=[CH:42][CH:41]=[C:40]([F:45])[C:39]=2[F:46])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 711173271-(4-Fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxylic acidHCID 86677557methyl(2,3,6-trifluorobenzylamino)-1H-imidazole-5-carboxylate

Product 1

HCID 711173261-(4-Fluorophenyl)-2-(methyl(2,3,6-trifluorobenzyl)amino)-1H-imidazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(4-Fluorophenyl)-2-(methyl(2,3,6-trifluorobenzyl)amino)-1H-imidazole-5-carboxylic acid (71) was prepared in a similar manner as that described for the synthesis of compound 11 using 1-(4-fluorophenyl)-2-(methyl(2,3,6-trifluorobenzylamino)-1H-imidazole-5-carboxylate (70) (24 mg, 0.061 mmol) and 1N LiOH (5 mL) in THF (5 mL) and MeOH (5 mL).

Sources & evidence

ORD record
ord-ce148f6ac5894a2ca56b3b65c9e99004
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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