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Isobutylamine → N-tert-Butyl-5-((4-(3-fluoro-4-(3-isobutylureido)benzoyl)piperazin-1-yl)methyl)furan-2-carboxamide

HRID 408858
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 408858
[NH2:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[O:19][C:18]([C:20]([NH:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)=[O:7])=[CH:4][C:3]=1[F:29].C(N(CC)C(C)C)(C)C.ClC(O[C:44](=[O:50])OC(Cl)(Cl)Cl)(Cl)Cl.[CH3:51][CH:52]([CH3:55])[CH2:53][NH2:54]>ClCCl>[C:23]([NH:22][C:20]([C:18]1[O:19][C:15]([CH2:14][N:11]2[CH2:10][CH2:9][N:8]([C:6](=[O:7])[C:5]3[CH:27]=[CH:28][C:2]([NH:1][C:44]([NH:54][CH2:53][CH:52]([CH3:55])[CH3:51])=[O:50])=[C:3]([F:29])[CH:4]=3)[CH2:13][CH2:12]2)=[CH:16][CH:17]=1)=[O:21])([CH3:26])([CH3:24])[CH3:25]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6558IsobutylamineHCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 666615235-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylfuran-2-carboxamide

Produkt 1

HCID 46182138N-tert-Butyl-5-((4-(3-fluoro-4-(3-isobutylureido)benzoyl)piperazin-1-yl)methyl)furan-2-carboxamideAusbeute 21,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylfuran-2-carboxamide (Example 3; 0.05 g, 0.124 mmol) and N,N-diisopropylethylamine (0.028 mL) were dissolved in dichloromethane (5 mL). Bis(trichloromethyl)carbonate (0.014 g, 0.046 mmol) was added dropwise and the reaction was left to stir for 30 minutes. N,N-diisopropylethylamine (0.094 mL) was added to the reaction followed by 2-methylpropan-1-amine (0.018 g, 0.248 mmol, 0.025 mL) and the reaction was stirred for a further 2 hours. The reaction mixture was washed with water and flushed through a hydrophobic frit. The organic phase was concentrated under vacuum and purified by basic reverse phase HPLC to afford the title compound (5 mg).

Aufarbeitung

  1. waitthe reaction was left
  2. stirringthe reaction was stirred for a further 2 hours
  3. washThe reaction mixture was washed with water
  4. customflushed through a hydrophobic frit
  5. concentrationThe organic phase was concentrated under vacuum
  6. custompurified by basic reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-f75fa8404add4a25bb32bcee93ef2dbd
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08759352B2

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