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

HRID 1878414
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HRID 1878414 반응식
[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
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344
Dichloromethane
용매

실험 절차

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]+

후처리

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

출처 및 근거

ORD 기록
ord-846035f8b355430c8e3f56e37426af41
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08314091B2

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