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 496748Notes

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

Participants

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

washThe solution was washed with saturated NaHCO3 solution
dry with materialdried over magnesium sulfate
customThe organic layer was evaporated to dryness
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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