4-Methylphenyl isocyanate → 3-[4-({[(4-Methylphenyl)amino]carbonyl}amino)phenyl]-5-{[(2-oxopyrrolidin-1-yl)carbonyl]amino}isothiazole-4-carboxamide

HRID 871009Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 871009
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([NH2:15])=[O:14])=[C:11]([NH:16][C:17]([N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])=[O:18])[S:10][N:9]=2)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:34]1([CH3:43])[CH:39]=[CH:38][C:37]([N:40]=[C:41]=[O:42])=[CH:36][CH:35]=1>CN(C)C=O.CCOC(C)=O>[CH3:43][C:34]1[CH:39]=[CH:38][C:37]([NH:40][C:41]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[C:12]([C:13]([NH2:15])=[O:14])=[C:11]([NH:16][C:17]([N:19]4[CH2:23][CH2:22][CH2:21][C:20]4=[O:24])=[O:18])[S:10][N:9]=3)=[CH:6][CH:7]=2)=[O:42])=[CH:36][CH:35]=1

Komponenten

6

Edukt 3

HCID 693254-Methylphenyl isocyanateHCID 81531DiisopropylethylamineHCID 716216283-(4-Aminophenyl)-5-{[(2-oxopyrrolidin-1-yl)carbonyl]amino}isothiazole-4-carboxamide

Produkt 1

HCID 716216293-[4-({[(4-Methylphenyl)amino]carbonyl}amino)phenyl]-5-{[(2-oxopyrrolidin-1-yl)carbonyl]amino}isothiazole-4-carboxamideAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 3-(4-aminophenyl)-5-{[(2-oxopyrrolidin-1-yl)carbonyl]amino}isothiazole-4-carboxamide (9.6 g, 0.027 mol), diisopropylethylamine (5.3 g, 0.046 mol) in dimethylformamide (150 mL) at ambient temperature was treated with para-Tolyl isocyanate (4.0 g 0.03 mol) over 20 minute period. The resulting mixture was stirred at ambient temperature for 2 hr. The reaction mixture was concentrated in vacuo to give an off white solid, which was stirred in EtOAc (150 mL), filtered the solid and washed with EtOAc to give the title compound as a white solid (11.8 g, 88%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give an off white solid, which
  3. filtrationfiltered the solid
  4. washwashed with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-23fabe61206a439991d8ed5c0f28c8aa
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969583B2

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