N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,3-propanediamine → N-[2-[[5-[(dimethylamino)methyl]furfuryl]thio]ethyl]-N'-[3-[N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]propyl]-2-nitro-1,1-ethenediamine
Reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]([CH2:14][CH2:15][N:16]([CH3:21])[CH2:17][CH2:18][CH2:19][NH2:20])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:24][N:25]([CH2:27][C:28]1[O:44][C:31]([CH2:32][S:33][CH2:34][CH2:35][NH:36][CH:37](SC)[CH2:38][N+:39]([O-:41])=[O:40])=[CH:30][CH:29]=1)[CH3:26]>>[CH3:26][N:25]([CH2:27][C:28]1[O:44][C:31]([CH2:32][S:33][CH2:34][CH2:35][NH:36][C:37]([NH:20][CH2:19][CH2:18][CH2:17][N:16]([CH2:15][CH2:14][N:7]([CH2:6][C:5]2[CH:22]=[CH:23][C:2]([F:1])=[CH:3][CH:4]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH3:21])=[CH:38][N+:39]([O-:41])=[O:40])=[CH:30][CH:29]=1)[CH3:24]Participants
3
Reactant 2
Product 1
Procedure
Preparation is effected analogously to Example 22, using 0.54 g (1.7 mmol) of N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,3-propanediamine and the equimolar amount of 1-[2-[[5-[(dimethylamino)methyl]furfuryl]thio]ethyl]amino-1-methylthio-2-nitroethane as starting materials. Working up by chromatography analogously to Example 22 yields the purified title compound in the form of a viscous oil; MS (+FAB method): m/z (rel. int. [%])=600 ([M+H]+, 12), 109 (100). For further analysis, a portion of the compound is converted into the tartaric acid salt in an ethanol/ether solvent mixture; m.p.: 63° C. (ethanol/ether).
Workup
- customPreparation
- customWorking up by chromatography analogously to Example 22 yields the
- custompurified title compound in the form of a viscous oil
Sources & evidence
- ORD record
- ord-cf85f5d1083646d9afa6edbebd4702fb
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05212187
Reaction notes
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