Methyl bromoacetate → HCID 72218457, compound

HRID 336358Notes

Reaction equation

HRID 336358 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[NH:21]1[CH:25]=[CH:24][N:23]=[N:22]1.[CH3:26][O:27][C:28](=[O:31])[CH2:29]Br>>[CH3:26][O:27][C:28](=[O:31])[CH2:29][N:21]1[CH:25]=[CH:24][N:23]=[N:22]1

Participants

5

Reactant 4

HCID 60984Methyl bromoacetateHCID 2733832Lithium HexamethyldisilazideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 178418936HCID 178418936, compound

Product 1

HCID 72218457HCID 72218457, compound

Procedure

Nitriles were reacted with LiHMDS or KHMDS to benzamidines which were converted to triazole by melting with hydrazides. The triazoles were coupled with 2-bromoacetic acid methyl ester under basic conditions to give the desired triazole-1-yl-acetic acid methyl ester together with different quantities of the isomeric systhem. The triazole-1-yl-acetic acid methyl ester was hydrolyzed with LiOH to the coresponding acid. The isomeres were either seperated before ore after hydrolysis of the ester. Finally, the triazole-1-yl-acetic acides were coupled with aryl substituted piperazines to the desired products.

Sources & evidence

ORD record
ord-227abdda659948d190b44de207f344fb
Source dataset
uspto-grants-2014_11
Patent number
US08889677B2

Reaction notes

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