Trifluoroacetic acid → 1-Cyclobutyl-3-(4-(piperazine-carbonyl)phenyl)urea

HRID 1878414Notes

Reaction equation

HRID 1878414 reaction equation
[CH:1]1([NH:5][C:6](=[O:29])[NH:7][C:8]2[CH:28]=[CH:27][C:11]([C:12]([N:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl.C(#N)C>[CH:1]1([NH:5][C:6]([NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]([N:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]3)=[O:13])=[CH:27][CH:28]=2)=[O:29])[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 57917609tert-Butyl 4-(4-(3-cyclobutylureido)benzoyl)piperazine-1-carboxylate

Product 1

HCID 579175741-Cyclobutyl-3-(4-(piperazine-carbonyl)phenyl)urea

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(4-(3-cyclobutylureido)benzoyl)piperazine-1-carboxylate (48.7 mmol, 19.6 g) was dissolved in a mixture of dichloromethane (125 ml) and acetonitrile (10 mL). After complete dissolution, trifluoroacetic acid (269 mmol, 20 mL, 30.7 g) was added over 10 minutes. The reaction was stirred until no trace of starting material remained. The reaction was neutralised with sodium hydrogen carbonate, filtered and concentrated under vacuum to generate a white solid. The desired product was isolated by continuous extraction of this material using soxhlet apparatus with dichloromethane as elutant. The organic phase was concentrated under vacuum to yield the title compound as a white powder (14.34 g). MS (ESI) m/z 303.5[M+H]+

Workup

  1. additionwas added over 10 minutes
  2. filtrationfiltered
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-846035f8b355430c8e3f56e37426af41
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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