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N,N'-bis-(2-amino-ethyl)-N,N'-dimethyl-propane-1,3-diamine → 6-[2-({3-[(2-Amino-ethyl)-methyl-amino]-propyl}-methyl-amino)-ethylamino]-3-methoxy-5,9-diaza-benzo[c]fluoren-7-one

HRID 496748
Notes
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Reaction equation

HRID 496748 reaction equation
Cl[C:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[N:10][CH:9]=[CH:8][C:7]=3[C:6]=2[C:5]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:4]=2[N:3]=1.[NH2:22][CH2:23][CH2:24][N:25]([CH3:34])[CH2:26][CH2:27][CH2:28][N:29]([CH2:31][CH2:32][NH2:33])[CH3:30]>ClCCl>[NH2:33][CH2:32][CH2:31][N:29]([CH3:30])[CH2:28][CH2:27][CH2:26][N:25]([CH3:34])[CH2:24][CH2:23][NH:22][C:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[N:10][CH:9]=[CH:8][C:7]=3[C:6]=2[C:5]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:4]=2[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 10607670N,N'-bis-(2-amino-ethyl)-N,N'-dimethyl-propane-1,3-diamineHCID 112549566-Chloro-3-methoxy-5,9-diaza-benzo[c]fluoren-7-one

Product 1

HCID 223220956-[2-({3-[(2-Amino-ethyl)-methyl-amino]-propyl}-methyl-amino)-ethylamino]-3-methoxy-5,9-diaza-benzo[c]fluoren-7-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 6-chloro-3-methoxy-5,9-diaza-benzo[c]fluoren-7-one (50.8 mg) (the compound of Reference Example 1c-2) and N,N′-bis-(2-amino-ethyl)-N,N′-dimethyl-propane-1,3-diamine (0.5 ml) was stirred at 50° C. for 4 hours. The reaction mixture was diluted with dichloromethane. The solution was washed with saturated NaHCO3 solution and dried over magnesium sulfate. The organic layer was evaporated to dryness. The residue was purified by silica gel column chromatography developed by dichloromethane-methanol-ammonia water (25%)=90:10:1. The desired product (49 mg) was obtained as a reddish oil.

Workup

  1. washThe solution was washed with saturated NaHCO3 solution
  2. dry with materialdried over magnesium sulfate
  3. customThe organic layer was evaporated to dryness
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-889f9e084efa4ca48a46f49902e7d839
Source dataset
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06946472B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes