Triethylamine → 4-(2-(3,5-bis-(4-Fluoro-phenyl)-(1,2,4)triazol-1-yl)-acetyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 239189Notes

Reaction equation

HRID 239189 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:25]=[C:24]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[N:23]([CH2:33][C:34](Cl)=[O:35])[N:22]=2)=[CH:17][CH:16]=1.C(N(CC)CC)C>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:34](=[O:35])[CH2:33][N:23]2[C:24]([C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)=[N:25][C:21]([C:18]3[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=3)=[N:22]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 86686520(3,5-bis-(4-Fluoro-phenyl)-(1,2,4)triazol-1-yl)-acetyl chloride

Product 1

HCID 866865224-(2-(3,5-bis-(4-Fluoro-phenyl)-(1,2,4)triazol-1-yl)-acetyl)-piperazine-1-carboxylic acid tert-butyl esterYield 66.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.8 g piperazine-1-carboxylic acid tert-butyl ester was added to 3.2 g (3,5-bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-acetyl chloride and 1 g triethylamine in 50 mL dichlormethane. The reaction was stirred for 1 day at RT, the solvent was evaporated and the residue was purified by chromatography on silica gel (petrolether/diethylether:1/1) to yield 3.1 g of the desired compound. Rt: 1.42 min (method B), (M+H)+: 484

Workup

  1. customthe solvent was evaporated
  2. customthe residue was purified by chromatography on silica gel (petrolether/diethylether:1/1)

Sources & evidence

ORD record
ord-c3001e83f283413ebbee6d82b85bb154
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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