1-chloro-N,N,2-trimethylpropylamine → (2,2-Dimethyl-piperazin-1yl)-[1-(3-fluoro-phenyl)-1H-[1,2,4]triazol-3yl]-methanone

HRID 334043Notes

Reaction equation

HRID 334043 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[N:11][C:10]([C:13]([OH:15])=O)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.ClC(N(C)C)C(C)C.C(OC([N:31]1[CH2:36][CH2:35][NH:34][C:33]([CH3:38])([CH3:37])[CH2:32]1)=O)(C)(C)C>C1COCC1>[CH3:37][C:33]1([CH3:38])[CH2:32][NH:31][CH2:36][CH2:35][N:34]1[C:13]([C:10]1[N:11]=[CH:12][N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[N:9]=1)=[O:15]

Participants

5

Reactant 3

HCID 202300821-chloro-N,N,2-trimethylpropylamineHCID 227103871-Boc-3,3-dimethylpiperazineHCID 866882381-(3-fluorophenyl)-1H-1,2,4-triazole-3-carboxylic acid

Product 1

HCID 86688275(2,2-Dimethyl-piperazin-1yl)-[1-(3-fluoro-phenyl)-1H-[1,2,4]triazol-3yl]-methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 460 mg (2.22 mmol) 1-(3-fluoro-phenyl)-1H-[1,2,4]-triazole-3-carboxylic acid and 330 μL (2.49 mmol) 1-chloro-N,N,2-trimethylpropylamine in 10 mL THF was stirred at RT for 30 min, 500 mg (2.22 mmol) 3,3-dimethyl-piperazine-1-carboxylic acid tert-butyl ester and 620 μL (4.45 mmol) TEA were added and the mixture was stirred at RT for 1 h. The solvent was removed by distillation and the residue was purified by HPLC.

Workup

  1. stirringthe mixture was stirred at RT for 1 h
  2. customThe solvent was removed by distillation
  3. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-003184d9d7ed44ad9e2a61aad4a7db4a
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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