N,N-Dimethylethylenediamine → HCID 178483769, compound

HRID 542535Notes

Reaction equation

HRID 542535 reaction equation
[CH:1]([C:3]1[C:16]([OH:17])=[CH:15][C:14]([OH:18])=[C:13]2[C:4]=1[N:5]=[C:6]1[C:11](=[N:12]2)[C:10]([C:19]([OH:21])=O)=[CH:9][CH:8]=[C:7]1[OH:22])=O.[C:23]([N:30]1[CH:34]=[CH:33][N:32]=[CH:31]1)(N1C=CN=C1)=O.[CH3:35][N:36]([CH3:40])[CH2:37][CH2:38][NH2:39]>CN(C)C=O>[CH3:31][N:30]([CH3:23])[CH2:34][CH2:33][NH:32][C:19]([C:10]1[C:11]2[C:6](=[N:5][C:4]3[C:13]([N:12]=2)=[C:14]([OH:18])[CH:15]=[C:16]([OH:17])[C:3]=3[CH:1]=[N:39][CH2:38][CH2:37][N:36]([CH3:40])[CH3:35])[C:7]([OH:22])=[CH:8][CH:9]=1)=[O:21]

Participants

5

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 178519907HCID 178519907, compound

Product 1

HCID 178483769HCID 178483769, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

6-Formyl-4,7,9-trihydroxy-1-phenazinecarboxylic acid (520 mg, 1.73 mmoles) was suspended in 15 ml of dry dimethylformamide (DMF) and 1,1'-carbonyldiimidazole (700 mg, 4.32 mmoles) dissolved in 4 ml of DMF was added. The reaction mixture was stirred for 20 minutes at 25° C. until a clear solution had formed. The solution was then cooled in an ice bath and N,N-dimethylethylenediamine (0.6 ml) added. After stirring for 15 minutes at 25° C. the excess reagents were removed under vacuum to yield N-[2-(dimethylamino)ethyl]-6-[[[2-(dimethylamino)ethyl]imino]methyl]-4,7,9-trihydroxy-1-phenazinecarboxamide. The retention time for this product in the HPLC system described above in Example 3 is 5.0 minutes.

Workup

  1. additionwas added
  2. customhad formed
  3. temperatureThe solution was then cooled in an ice bath
  4. stirringAfter stirring for 15 minutes at 25° C. the excess reagents
  5. customwere removed under vacuum

Sources & evidence

ORD record
ord-a83da663814e4ca9a2fe10c364efd411
Source dataset
uspto-grants-1987_04
Patent number
US04657909

Reaction notes

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