N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,6-hexanediamine → N-cyano-N'-[2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethyl]-N"-[6-[N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]hexyl]-guanidine

HRID 249002Notes

Reaction equation

HRID 249002 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]([CH2:15][CH2:16][N:17]([CH3:25])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[C:28]([NH:30][C:31](=[N:39][CH2:40][CH2:41][S:42][CH2:43][C:44]1[N:45]=[C:46]([NH:49][C:50]([NH2:52])=[NH:51])[S:47][CH:48]=1)OC1C=CC=CC=1)#[N:29]>>[C:28]([NH:30][C:31]([NH:39][CH2:40][CH2:41][S:42][CH2:43][C:44]1[N:45]=[C:46]([NH:49][C:50]([NH2:52])=[NH:51])[S:47][CH:48]=1)=[N:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH2:16][CH2:15][N:8]([CH2:7][C:6]1[CH:26]=[CH:27][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[CH3:25])#[N:29]

Participants

3

Reactant 2

HCID 19762600N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,6-hexanediamineHCID 178512334HCID 178512334, compound

Product 1

HCID 178491100N-cyano-N'-[2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethyl]-N"-[6-[N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]hexyl]-guanidine

Procedure

Preparation is effected analogously to Example 1, using 0.57 g (1.5 mmol) of N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,6-hexanediamine and the equimolar amount of N-cyano-N'-[2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethyl]-O-phenyl-isourea as starting materials. Working up by chromatography analogously to Example 1 yields the purified title compound in the form of a viscous oil that crystallises from ether at -20° C.; MS (+FAB method): m/z (rel. int. [%])=652 ([M+H]+, 12), 121 (100); IR (KBr): 2162 cm-1 (C≡N); m.p.: 52° C. (ether).

Workup

  1. customPreparation
  2. customWorking up by chromatography analogously to Example 1 yields the
  3. custompurified title compound in the form of a viscous oil
  4. customthat crystallises from ether at -20° C.

Sources & evidence

ORD record
ord-03e4aad598634f238bfc4db1a8194969
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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