4-Bromo-2-methylphenyl isocyanate → N-(4-Bromo-2-methylphenyl)-2-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetyl}hydrazinecarboxamide

HRID 525160Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 525160
[CH:1]1([C:4]([N:6]2[CH2:10][CH2:9][C@@H:8]([CH2:11][C:12]([NH:14][NH2:15])=[O:13])[CH2:7]2)=[O:5])[CH2:3][CH2:2]1.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[C:19]([CH3:26])[CH:18]=1>ClCCl>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:15][NH:14][C:12](=[O:13])[CH2:11][C@@H:8]2[CH2:9][CH2:10][N:6]([C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:5])[CH2:7]2)=[O:25])=[C:19]([CH3:26])[CH:18]=1

Komponenten

4

Edukt 2

HCID 27355944-Bromo-2-methylphenyl isocyanateHCID 673540782-[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetohydrazide

Produkt 1

HCID 71087270N-(4-Bromo-2-methylphenyl)-2-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetyl}hydrazinecarboxamideAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetohydrazide (800 mg, 3.79 mmol) in dry dichloromethane (5 mL) was added 4-bromo-1-isocyanato-2-methylbenzene (803 mg, 3.79 mmol). The reaction was allowed to progress for 1 h at room temperature (became a thick suspension that could not be stirred). The reaction mixture was diluted with dichloromethane (10 mL) and the precipitate was collected by filtration. A second crop was obtained by filtration and the two crops were combined, rinsed with minimal dichloromethane and dried to constant weight under high vacuum to provide the title product (1.54 g, 3.64 mmol, 96% yield) as a white solid. MS(ES)+ m/e 422.9 [M+H]+. This material was 76% pure by LCMS (UV214) and was used as is in the next step.

Aufarbeitung

  1. filtrationthe precipitate was collected by filtration
  2. customA second crop was obtained by filtration
  3. washrinsed with minimal dichloromethane
  4. customdried to constant weight under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-cba9cc2622d34d13af5e77aa522fd125
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340529B2

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