Ethylenediamine → 3,5-diamino-N-[2-[[2-[(2-aminoethyl)amino]2-oxoethyl]amino]ethyl]-6-chloropyrazinecarboxamide

HRID 1164833Notes

Reaction equation

HRID 1164833 reaction equation
CO[C:3](=[O:20])[CH2:4][NH:5][CH2:6][CH2:7][NH:8][C:9]([C:11]1[C:16]([NH2:17])=[N:15][C:14]([NH2:18])=[C:13]([Cl:19])[N:12]=1)=[O:10].[CH2:21]([NH2:24])[CH2:22][NH2:23]>>[NH2:17][C:16]1[C:11]([C:9]([NH:8][CH2:7][CH2:6][NH:5][CH2:4][C:3]([NH:23][CH2:22][CH2:21][NH2:24])=[O:20])=[O:10])=[N:12][C:13]([Cl:19])=[C:14]([NH2:18])[N:15]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 19863354N-[2-[[(3,5-diamino-6-chloropyrazinyl)carbonyl]amino]ethyl]glycine methyl ester

Product 1

HCID 198633533,5-diamino-N-[2-[[2-[(2-aminoethyl)amino]2-oxoethyl]amino]ethyl]-6-chloropyrazinecarboxamideYield 100%

Procedure

A solution of 7.45 g (24.6 mmol) of N-[2-[[(3,5-diamino-6-chloropyrazinyl)carbonyl]amino]ethyl]glycine methyl ester and 22.48 ml (373.9 mmol) of ethylenediamine was stirred at ambient temperature for two days. The excess diamine was evaporated. There was obtained 8.14 g (24.6 mmol, 100%) of 3,5-diamino-N-[2-[[2-[(2-aminoethyl)amino]2-oxoethyl]amino]ethyl]-6-chloropyrazinecarboxamide as a yellow solid: Rf=0.28, Solvent System A.

Workup

  1. customThe excess diamine was evaporated

Sources & evidence

ORD record
ord-270fdc30c4f84827880bc56fde7b79da
Source dataset
uspto-grants-1990_03
Patent number
US04906633

Reaction notes

Loading…