Trifluoroacetic acid → N-tert-butyl-5-(piperazin-1-ylmethyl)furan-2-carboxamide

HRID 408855Notes

Reaction equation

HRID 408855 reaction equation
[C:1]([NH:5][C:6]([C:8]1[O:12][C:11]([CH2:13][N:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([NH:5][C:6]([C:8]1[O:12][C:11]([CH2:13][N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66661701tert-Butyl 4-((5-(tert-butylcarbamoyl)furan-2-yl)methyl)piperazine-1-carboxylate

Product 1

HCID 66661240N-tert-butyl-5-(piperazin-1-ylmethyl)furan-2-carboxamideYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 4-((5-(tert-butylcarbamoyl)furan-2-yl)methyl)piperazine-1-carboxylate (6.57 mmol, 2.4 g) was dissolved in dichloromethane (20 mL). 2,2,2-Trifluoro-acetic acid (20 mL) was added and the reaction mixture was stirred for 2 hours. The reaction was concentrated under reduced pressure and purified by SCX chromatography to give the title compound (1.51 g). MS (ESI) m/z 266.4 [M+H]+

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. custompurified by SCX chromatography

Sources & evidence

ORD record
ord-69a8fbdc2584495380a503635bde4224
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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