Lithium Hydroxide → 2-((2-Chloro-6-fluorophenyl)ethynyl)-1-(4-fluorophenyl)-1H-imidazole-5-carboxylic acid

HRID 2368503Notes

Reaction equation

HRID 2368503 reaction equation
CN1C=C(CN(C)C(C2N(C3C=CC(F)=CC=3)C(S)=NC=2)=O)C(C)=N1.[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:28]=1[C:34]#[C:35][C:36]1[N:37]([C:46]2[CH:51]=[CH:50][C:49]([F:52])=[CH:48][CH:47]=2)[C:38]([C:41]([O:43]CC)=[O:42])=[CH:39][N:40]=1.[OH-].[Li+].C1COCC1>O.CO>[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:28]=1[C:34]#[C:35][C:36]1[N:37]([C:46]2[CH:47]=[CH:48][C:49]([F:52])=[CH:50][CH:51]=2)[C:38]([C:41]([OH:43])=[O:42])=[CH:39][N:40]=1

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 71119630ethyl 2-((2-chloro-6-fluorophenyl)ethynyl)-1-(4-fluorophenyl)-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 711175772-((2-Chloro-6-fluorophenyl)ethynyl)-1-(4-fluorophenyl)-1H-imidazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-((2-Chloro-6-fluorophenyl)ethynyl)-1-(4-fluorophenyl)-1H-imidazole-5-carboxylic acid (43) was prepared in a similar manner as that described for the synthesis of compound 7 using ethyl 2-((2-chloro-6-fluorophenyl)ethynyl)-1-(4-fluorophenyl)-1H-imidazole-5-carboxylate (42) (44 mg, 0.11 mmol), lithium hydroxide (11 mg, 0.46 mmol), THF (0.1 mL), methanol (0.2 mL), and water (0.4 mL).

Sources & evidence

ORD record
ord-207b90a891814c2fbbe57666d3cf15eb
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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