Trifluoroacetic acid → N-tert-Butyl-2-(piperazin-1-ylmethyl)thiazole-4-carboxamide

HRID 408850Notes

Reaction equation

HRID 408850 reaction equation
[C:1]([NH:5][C:6]([C:8]1[N:9]=[C:10]([CH2:13][N:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)[S:11][CH:12]=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[N:9]=[C:10]([CH2:13][N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[S:11][CH:12]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66661726tert-Butyl 4-((4-(tert-butylcarbamoyl)thiazol-2-yl)methyl)piperazine-1-carboxylate

Product 1

HCID 66661281N-tert-Butyl-2-(piperazin-1-ylmethyl)thiazole-4-carboxamideYield 82.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 4-((4-(tert-butylcarbamoyl)thiazol-2-yl)methyl)piperazine-1-carboxylate (2.1 g, 5.49 mmol) was dissolved in dichloromethane (20 mL). 2,2,2-Trifluoracetic 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 column chromatography to give the title compound (1.28 g). MS (ESI) m/z 283.4 [M+H]+

Workup

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

Sources & evidence

ORD record
ord-ba3a425f0d1b4324b8f7b59c9a3ffed0
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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