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

HRID 968282Notes

Reaction equation

HRID 968282 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-c1c974728dc24fe3b2823898ff0d555f
Source dataset
uspto-grants-2005_10
Patent number
US06958347B2

Reaction notes

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