N,N-Dimethylethylenediamine → 4-Methoxy-benzo[a]phenazine-11-carboxylic acid (2-dimethylamino-ethyl)-amide

HRID 719188Notes

Reaction equation

HRID 719188 reaction equation
[CH3:1][O:2][C:3]1[C:8]2=[CH:9][CH:10]=[C:11]3[C:20]([N:19]=[C:18]4[C:13]([CH:14]=[CH:15][CH:16]=[C:17]4[C:21]([OH:23])=O)=[N:12]3)=[C:7]2[CH:6]=[CH:5][CH:4]=1.[C:24](N1C=CN=C1)([N:26]1[CH:30]=[CH:29][N:28]=[CH:27]1)=O.CN(C)CCN>CN(C)C=O>[CH3:24][N:26]([CH3:27])[CH2:30][CH2:29][NH:28][C:21]([C:17]1[C:18]2[C:13](=[N:12][C:11]3[C:20]([N:19]=2)=[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]2=[CH:9][CH:10]=3)[CH:14]=[CH:15][CH:16]=1)=[O:23]

Participants

5

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 111202464-Methoxy-benzo[a]phenazine-11-carboxylic Acid

Product 1

HCID 99514874-Methoxy-benzo[a]phenazine-11-carboxylic acid (2-dimethylamino-ethyl)-amideYield 75.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-methoxy-benzo[a]phenazine-11-carboxylic acid (II.1) (129 mg) and 1,1′-carbonyldiimidazole (138 mg) was stirred in dry N,N-dimethylformamide (8 mL) at room temperature for 4 hours. To this mixture was added N,N-dimethylethylenediamine (commercially available)(0.5 mL) and the reaction mixture was stirred at room temperature for a further 30 minutes. The volatiles were then removed in vacuo. The residue was dissolved in dichloromethane, washed with water, dried (MgSO4) and the solvent removed in vacuo to provide crude product. This was purified using flash chromatography (5% methanol in dichloromethane) to yield the title compound as a bright yellow solid (120 mg).

Workup

  1. customThe volatiles were then removed in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto provide crude product
  7. customThis was purified

Sources & evidence

ORD record
ord-06b9bb860ac248ab8255d7e537064d54
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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