Reaction equation
[F:1][C:2]([F:20])([F:19])[CH2:3][N:4]=[C:5]([NH2:18])[NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])[N:11]=1.C[O:22][C:23]1[C:26](=O)[C:25](=O)[C:24]=1[O:29]C.[CH3:31][NH2:32]>CO>[F:20][C:2]([F:1])([F:19])[CH2:3][N:4]=[C:5]([NH2:18])[NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:26]2[C:23](=[O:22])[C:24](=[O:29])[C:25]=2[NH:32][CH3:31])[N:11]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 2-[2-(2,2,2-trifluoroethyl)guanidino]-4-(5-aminopentyl)thiazole (0.3 g.) and 1,2-dimethoxycyclobutene-3,4-dione (0.15 g.) in methanol (3 ml.) was allowed to stand at room temperature for 4 hours. Ethanolic methylamine (33% w/v, 20 ml.) was then added and the solution allowed to stand overnight. The mixture was evaporated to dryness and the residue purified by preparative thin layer chromatography using ethyl acetate/methanol/water 6:1:1 v/v/v as developing solvent to give 1-[5-(2-[2-(2,2,2-trifluoroethyl)guanidino]thiazol-4-yl)pentylamino]-2-methylaminocyclobutene-3,4-dione as colourless gum (0.17 g.). The n.m.r. spectrum of the hydrogen maleate salt in d6 dimethylsulphoxide using tetramethylsilane as internal standard (δ=0) included the following resonances (67 ): 1.5 (multiplet, 6H); 2.6 (multiplet, 2H); 3.1 (doublet, 3H); 3.5 (multiplet, 2H); 4.1 (multiplet, 2H); 6.55 (singlet, 1H).
Workup
- waitto stand overnight
- customThe mixture was evaporated to dryness
- customthe residue purified by preparative thin layer chromatography
Sources & evidence
- ORD record
- ord-335189b9479842b58b044dd68bd8c7fe
- Source dataset
- uspto-grants-1988_08
- Patent number
- US04762932
Linked notes
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