Cyclopropylamine → HCID 67432850, Verbindung

HRID 2036612Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2036612
Br[C:2]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([NH:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[CH:18]1([NH2:21])[CH2:20][CH2:19]1>C1COCC1.CCOC(C)=O>[C:7]([NH:6][C:4](=[O:5])[C:3]1[CH:11]=[CH:12][CH:13]=[C:14]([N+:15]([O-:17])=[O:16])[C:2]=1[NH:21][CH:18]1[CH2:20][CH2:19]1)([CH3:10])([CH3:9])[CH3:8]

Komponenten

5

Edukt 2

HCID 69828CyclopropylamineHCID 674309942-bromo-N-tert-butyl-3-nitrobenzamide

Produkt 1

HCID 67432850HCID 67432850, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 2-bromo-N-tert-butyl-3-nitrobenzamide (460 mg, 1.52 mmol) and cyclopropanamine (350 μL, 4.55 mmol) in THF (10 mL) was heated at 60° C. for 18 h. The reaction mixture was diluted with EtOAc, washed with water, brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using EtOAC:DCM (1:1) as eluent to give N-tert-butyl-2-(cyclopropylamino)-3-nitrobenzamide: 1H NMR (400 MHz, CDCl3) δ 8.26 (1H, br), 8.09 (1H, dd, J=8.0, 4.0 Hz), 7.57 (1H, d, J=8.0 Hz), 6.72 (1H, t, J=8.0 Hz), 5.81 (1H, br), 2.98-2.92 (1H, m), 1.49 (9H, s), 0.82-0.76 (2H, m), 0.58-0.52 (2H, m); LC-MS (ESI) m/z 278.2 [M+H]+.

Aufarbeitung

  1. washwashed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel using EtOAC

Quellen und Nachweise

ORD-Eintrag
ord-89f11ad4778a46868bbd34d3bcb46ef6
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575183B2

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