2-fluoro-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide → HCID 178522768, Verbindung

HRID 1934645

Reaktionsgleichung

Reaktionsgleichung von HRID 1934645
F[C:2]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:16]=[CH:15][C:11]2[O:12][CH2:13][O:14][C:10]=2[CH:9]=1)=[O:5].[NH2:24][C@H:25]1[CH2:30][CH2:29][C@H:28]([OH:31])[CH2:27][CH2:26]1>N1C=CC=CC=1>[OH:31][C@H:28]1[CH2:29][CH2:30][C@H:25]([NH:24][C:2]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:3]=2[C:4]([NH:6][CH2:7][C:8]2[CH:16]=[CH:15][C:11]3[O:12][CH2:13][O:14][C:10]=3[CH:9]=2)=[O:5])[CH2:26][CH2:27]1

Komponenten

4

Edukt 2

HCID 224676412-fluoro-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamideHCID 178511715HCID 178511715, Verbindung

Produkt 1

HCID 178522768HCID 178522768, VerbindungAusbeute 84,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of 2-fluoro-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide (150 mg) in anhydrous pyridine (3 mL) was added trans-4-aminocyclohexanol (81.4 mg), and the mixture was stirred for 15 hours at ambient temperature, and then for 3 hours at 60° C. The mixture was partitioned between ethyl acetate and water. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was subjected to a silica gel column chromatography eluting with a mixture of chloroform and methanol (20:1). The eluent was concentrated and the residue was triturated with diisopropyl ether to give 2-(trans-4-hydroxycyclohexylamino)-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide as yellow powders (164 mg).

Aufarbeitung

  1. waitfor 3 hours at 60° C
  2. customThe mixture was partitioned between ethyl acetate and water
  3. washThe separated organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. washeluting with a mixture of chloroform and methanol (20:1)
  7. concentrationThe eluent was concentrated
  8. customthe residue was triturated with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-51cea3d5a0df4652af0750f4f91785be
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06384080B1

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