Ethylenediamine → HCID 178512327, compound

HRID 364312Notes

Reaction equation

HRID 364312 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. resonanes 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-0657c0b3dc5d4c8aa169009162094bb4
Source dataset
uspto-grants-1986_08
Patent number
US04604465

Reaction notes

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