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

HRID 968290Notes

Reaction equation

HRID 968290 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

HCID 222885432-Dimethylamino-N-(5-methyl-6-oxo-5,6-dihydro-phenanthridin-8-yl)-acetamideYield 33.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

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 residue was purified by rotary chromatography on silica gel (dichloromethane grading to 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-6f04bccc9ed547e386572b052de4c88a
Source dataset
uspto-grants-2005_10
Patent number
US06958347B2

Reaction notes

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