N,N-bis(3-aminopropyl)methylamine → 6-(3-{methyl-[3-(7-oxo-7H-5,9-diaza-benzo[c]fluoren-6-ylamino)-propyl]-amino}-propylamino)-5,9-diaza-benzo[c]fluoren-7-one

HRID 496741

Reaction equation

HRID 496741 reaction equation
[O:1]=[C:2]1[C:14]2[C:13](OS(C3C=CC(C)=CC=3)(=O)=O)=[N:12][C:11]3[CH:26]=[CH:27][CH:28]=[CH:29][C:10]=3[C:9]=2[C:8]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]1=2.[NH2:30][CH2:31][CH2:32][CH2:33][N:34]([CH3:39])[CH2:35][CH2:36][CH2:37][NH2:38].[C:40](=[O:43])([O-])[O-].[K+].[K+]>ClCCl>[CH3:39][N:34]([CH2:35][CH2:36][CH2:37][NH:38][C:13]1[C:14]2[C:40](=[O:43])[C:3]3[CH:4]=[N:5][CH:6]=[CH:7][C:8]=3[C:9]=2[C:10]2[CH:29]=[CH:28][CH:27]=[CH:26][C:11]=2[N:12]=1)[CH2:33][CH2:32][CH2:31][NH:30][C:13]1[C:14]2[C:2](=[O:1])[C:3]3[CH:4]=[N:5][CH:6]=[CH:7][C:8]=3[C:9]=2[C:10]2[CH:29]=[CH:28][CH:27]=[CH:26][C:11]=2[N:12]=1

Participants

5

Reactant 3

HCID 7777N,N-bis(3-aminopropyl)methylamineHCID 11430Potassium CarbonateHCID 20829786HCID 20829786, compound

Product 1

HCID 103938896-(3-{methyl-[3-(7-oxo-7H-5,9-diaza-benzo[c]fluoren-6-ylamino)-propyl]-amino}-propylamino)-5,9-diaza-benzo[c]fluoren-7-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of toluene-4-sulfonic acid 7-oxo-7H-5,9-diaza-benzo[c]fluoren-6-yl ester (Reference Example 6c-2) (90 mg) and N1-(3-amino-propyl)-N1-methyl-propane-1,3-diamine (WAKO PURE CHEMICAL: 15 mg) and potassium carbonate (37 mg) was suspended in dichloromethane (10 ml) and heated at reflux temperature for five days under nitrogen. The mixture was roughly purified by short silica gel column chromatography developed by dichloromethane-methanol=100:1 and dichloromethane-methanol=1:1. The fractions that contained the desired product were combined and evaporated to dryness and purified again by silica gel thin layer chromatography developed by dichloromethane-methanol-ammonia water=90:10:1. The desired compound was obtained as a dark reddish powder.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for five days under nitrogen
  3. customThe mixture was roughly purified by short silica gel column chromatography
  4. customevaporated to dryness
  5. custompurified again by silica gel thin layer chromatography

Sources & evidence

ORD record
ord-47ebe698c6114793aab8c2c5be8b4eb9
Source dataset
uspto-grants-2005_09
Patent number
US06946472B2

Linked notes

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