Methyl Isocyanate → N-methyl-N'-(3-(octahydroindolizin-7-yl)-1H-indol-5-yl)urea

HRID 363334Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 363334
[CH3:1][N:2]=[C:3]=[O:4].[CH2:5]1[CH:13]2[N:8]([CH2:9][CH2:10][CH:11]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([NH2:23])[CH:21]=4)[NH:16][CH:15]=3)[CH2:12]2)[CH2:7][CH2:6]1>CN(C)C=O>[CH3:1][NH:2][C:3]([NH:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH:11]1[CH2:12][CH:13]2[N:8]([CH2:7][CH2:6][CH2:5]2)[CH2:9][CH2:10]1)=[O:4]

Komponenten

4

Edukt 2

HCID 12228Methyl IsocyanateHCID 153897613-(Octahydroindolizin-7-yl)-5-amino-1H-indole

Produkt 1

HCID 44214635N-methyl-N'-(3-(octahydroindolizin-7-yl)-1H-indol-5-yl)ureaAusbeute 55,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The methylisocyanate (220 mg, 3.9 mmol) was added to a solution of 3-(octahydroindolizin-7-yl)-5-amino-1H-indole (500 mg, 1.95 mmol) in 10 ml of dimethylformamide. The reaction was allowed to stir for 72 hours. TLC indicated the reaction was complete so the reaction was concentrated to give a purple gum. This material was chromatographed on a short FLORISIL™ column using 20% methanol in methylene chloride (ammonium hydroxide) as solvent to give 340 mg of a white foam. The white foam was recrystallized from methanol/ethyl acetate to give 165 mg of product. (27.1%).

Aufarbeitung

  1. concentrationwas concentrated
  2. customto give a purple gum
  3. customThis material was chromatographed on a short FLORISIL™ column

Quellen und Nachweise

ORD-Eintrag
ord-8c71a29d084146508f997148f0da02f6
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05874427

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