Ethylenediamine → HCID 178512327, compound

HRID 1902314Notes

Reaction equation

HRID 1902314 reaction equation
[F:1][C:2]([F:26])([F:25])[CH2:3][N:4]=[C:5]([NH2:24])[NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[N:21][C:22]#[N:23])SC)[N:11]=1.[NH2:27][CH2:28][CH2:29][NH2:30]>C(O)C>[F:1][C:2]([F:26])([F:25])[CH2:3][N:4]=[C:5]([NH2:24])[NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([NH:21][C:22]#[N:23])=[N:27][CH2:28][CH2:29][NH2:30])[N:11]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 178503913HCID 178503913, compound

Product 1

HCID 178512327HCID 178512327, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-[2-(2,2,2-trifluoroethyl)-guanidino]-4-[5-(3-cyano-2-methylisothioureido)pentyl]-thiazole (0.5 g.) and 1,2-diaminoethane (1.5 ml.) in ethanol (1 ml.) was allowed to stand at room temperature overnight. The mixture was then evaporated to dryness and the residue purified by preparative medium pressure liquid chromatography on silica gel using methanol/chloroform 1:4 v/v as solvent to give 2-[2-(2,2,2-trifluoroethyl)guanidino]-4-[5-(3-cyano-2-[2-aminoethyl]guanidino)pentyl]thiazole as a straw coloured gum. A sample of the salt prepared with maleic acid included the following n.m.r. resonances when examined in d6 dimethylsulphoxide containing tetramethylsilane as an internal standard (δ=0) (δ):-1.5 (multiplet, 6H); 3.0 (multiplet, 4H); 3.3 (multiplet, 2H); 4.1 (multiplet, 2H); 6.5 (singlet, 1H).

Workup

  1. customThe mixture was then evaporated to dryness
  2. customthe residue purified by preparative medium pressure liquid chromatography on silica gel

Sources & evidence

ORD record
ord-7c0749d5514d49ca8b25f7ef394f22b0
Source dataset
uspto-grants-1982_12
Patent number
US04362728

Reaction notes

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