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N,N-Dimethylglycine → 2-Dimethylamino-N-(5-methyl-6-oxo-5,6-dihydro-phenanthridin-8-yl)-acetamide

HRID 968290
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 968290
Cl.CN(C)CCCN=C=NCC.[NH2:13][C:14]1[CH:15]=[C:16]2[C:25](=[CH:26][CH:27]=1)[C:24]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:18]([CH2:28]C)[C:17]2=[O:30].[CH3:31][N:32]([CH3:37])[CH2:33][C:34](O)=[O:35].C(N(CC)CC)C>ClCCl>[CH3:31][N:32]([CH3:37])[CH2:33][C:34]([NH:13][C:14]1[CH:15]=[C:16]2[C:25](=[CH:26][CH:27]=1)[C:24]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:18]([CH3:28])[C:17]2=[O:30])=[O:35]
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Komponenten

6

Edukt 4

HCID 673N,N-DimethylglycineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 222885418-amino-5-ethyl-5H-phenanthridin-6-one

Produkt 1

HCID 222885432-Dimethylamino-N-(5-methyl-6-oxo-5,6-dihydro-phenanthridin-8-yl)-acetamideAusbeute 33,5 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC) (63 mg, 0.33 mmol) was added in one portion to a solution of 8-amino-5-ethyl-5H-phenanthridin-6-one I-16c (65 mg, 0.27 mmol), N,N-dimethylglycine (34 mg, 0.33 mmol) 4-dimethylaminopyridine (7 mg, 0.054 mmol), and triethylamine (0.076 ml, 0.55 mmol) in dichloromethane (5 ml). The resultant solution was stirred at 23° C. for 16 hours and diluted with 1:1 ethyl acetate/hexanes (20 ml). The reaction mixture was washed with water (25 ml) and saturated aqueous ammonium chloride (25 ml) and dried over anhydrous magnesium sulfate and concentrated. The residue was purified by rotary chromatography on silica gel (dichloromethane grading to 5% methanol/dichloromethane) to provide 2-dimethylamino-N-(5-methyl-6-oxo-5,6-di hydro-phenanthridin-8-yl)-acetamide 16A (28 mg, 33%) as a yellow oil.

Aufarbeitung

  1. washThe reaction mixture was washed with water (25 ml) and saturated aqueous ammonium chloride (25 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by rotary chromatography on silica gel (dichloromethane grading to 5% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-6f04bccc9ed547e386572b052de4c88a
Quelldatensatz
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06958347B2

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