Triethylamine → N-(5-Ethyl-6-oxo-5,6-dihydro-phenanthridin-9-yl)-2-pyridin-4-yl-acetamide

HRID 968282Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968282
Cl.CN(C)[CH2:4][CH2:5][CH2:6]N=C=NCC.[NH2:13][C:14]1[CH:27]=[C:26]2[C:17]([C:18](=[O:30])[N:19]([CH2:28][CH3:29])[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=32)=[CH:16][CH:15]=1.[OH:31]N1C2C=CC=CC=2N=N1.C([N:43]([CH2:46][CH3:47])[CH2:44][CH3:45])C>ClCCl.C(OCC)(=O)C>[CH2:28]([N:19]1[C:18](=[O:30])[C:17]2[C:26](=[CH:27][C:14]([NH:13][C:4](=[O:31])[CH2:5][C:6]3[CH:45]=[CH:44][N:43]=[CH:46][CH:47]=3)=[CH:15][CH:16]=2)[C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]1=2)[CH3:29]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 103993089-amino-5-ethyl-5H-phenanthridin-6-one

Produkt 1

HCID 10247746N-(5-Ethyl-6-oxo-5,6-dihydro-phenanthridin-9-yl)-2-pyridin-4-yl-acetamideAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC) (962 mg, 5.03 mmol) was added in one portion to a solution of 9-amino-5-ethyl-5H-phenanthridin-6-one 1A (1.0 g, 4.2 mmol), 1-hydroxybenzotriazole (850 mg, 6.3 mmol), and triethylamine (0.64 ml, 4.6 mmol) in dichloromethane (20 ml). The resultant solution was stirred at 23° C. for 16 hours and diluted with ethyl acetate (50 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 solid residue was triturated with methanol to provide N-(5-ethyl-6-oxo-5,6-dihydro-phenanthridin-9-yl)-2-pyridin-4-yl-acetamide 5A (509 mg, 34%).

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 solid residue was triturated with methanol

Quellen und Nachweise

ORD-Eintrag
ord-c1c974728dc24fe3b2823898ff0d555f
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06958347B2

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