Carbon Disulfide → HCID 178491102, compound

HRID 249018Notes

Reaction equation

HRID 249018 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.C1(N=C=NC2CCCCC2)CCCCC1.[NH:43]([C:47]1[S:48][CH:49]=[C:50]([CH2:52][S:53][CH2:54][CH2:55][NH2:56])[N:51]=1)[C:44]([NH2:46])=[NH:45].[C:57](=S)=[S:58]>CCOCC.C(O)C>[NH:43]([C:47]1[S:48][CH:49]=[C:50]([CH2:52][S:53][CH2:54][CH2:55][NH:56][C:57]([NH: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]2[CH:26]=[CH:27][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH3:25])=[S:58])[N:51]=1)[C:44]([NH2:46])=[NH:45]

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 10868DicyclohexylcarbodiimideHCID 19762600N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,6-hexanediamineHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178491102HCID 178491102, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

0.48 g (1.3 mmol) of N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,6-hexanediamine and 0.27 g (1.3 mmol) of dicyclohexylcarbodiimide are dissolved at -10° C. in absolute ether with 0.5 ml of carbon disulfide, the temperature is increased in the course of 3 hours to 20° C. and the batch is stirred for a further 12 hours. The solid that precipitates is filtered off and the filtrate is concentrated in vacuo. 0.30 g (1.3 mmol) of 2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethaneamine dissolved in a small amount of absolute ethanol is added to the concentrated residue and the reaction batch is heated under reflux for 2 hours. It is then concentrated in vacuo and the residue is purified by rotation chromatography to yield the purified title compound in the form of a viscous oil; MS (+FAB method): m/z (rel. int. [%])=644 ([M+H]+, 1), 121 (100). For further analysis, a portion of the compound is converted into the tartaric acid salt and recrystallised from acetonitrile/isopropanol/petroleum ether; m.p.: 78° C. (acetonitrile/isopropanol/petroleum ether).

Workup

  1. temperaturethe temperature is increased in the course of 3 hours to 20° C.
  2. customThe solid that precipitates
  3. filtrationis filtered off
  4. concentrationthe filtrate is concentrated in vacuo
  5. additionis added to the concentrated residue
  6. temperaturethe reaction batch is heated
  7. temperatureunder reflux for 2 hours
  8. concentrationIt is then concentrated in vacuo
  9. customthe residue is purified by rotation chromatography
  10. customto yield the
  11. custompurified title compound in the form of a viscous oil
  12. customrecrystallised from acetonitrile/isopropanol/petroleum ether

Sources & evidence

ORD record
ord-655f31a5490d4c1084f13bc62ce511be
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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