Maleic Acid → Maleic Acid

HRID 1902310Notes

Reaction equation

HRID 1902310 reaction equation
[F:1][C:2]([F:19])([F:18])[CH2:3][N:4]=[C:5]([NH2:17])[NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])[N:11]=1.[N+](N[C:24]1[NH:29][C:28](=[O:30])[C:27]([CH3:31])=[CH:26][N:25]=1)([O-])=O.[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]\[C:35]([OH:37])=[O:36]>N1C=CC=CC=1.CC(C)=O>[CH3:31][C:27]1[C:28](=[O:30])[NH:29][C:24]([NH:16][CH2:15][CH2:14][CH2:13][CH2:12][C:10]2[N:11]=[C:7]([NH:6][C:5]([NH2:17])=[N:4][CH2:3][C:2]([F:1])([F:18])[F:19])[S:8][CH:9]=2)=[N:25][CH:26]=1.[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]\[C:35]([OH:37])=[O:36]

Participants

7

Reactant 3

HCID 444266Maleic AcidHCID 212987102-[2-(2,2,2-Trifluoroethyl)-guanidino]-4-(4-aminobutyl)thiazoleHCID 212987932-nitroamino-5-methyl-4(3H)-pyrimidone

Product 2

HCID 444266Maleic AcidHCID 212987425-Methyl-2-(4-[(-2-[2,2,2-trifluoroethyl]guanidino)thiazol-4-yl]butylamino)pyrimid-4-one

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1049PyridineSolvent

Procedure

A mixture of 2-[2-(2,2,2-trifluoroethyl)-guanidino]-4-(4-aminobutyl)thiazole (0.7 g.) and 2-nitroamino-5-methyl-4(3H)-pyrimidone (0.3 g.) was heated under reflux in pyridine (3 ml.) for 3.5 hours. The mixture was then evaporated to dryness and the residue purified by preparative thin layer chromatography using ethyl acetate/methanol 6:1:1 v/v/v for development. The appropriate band was extracted with chloroform/ethanol 1:1 v/v (200 ml.). Evaporation of the solvent to dryness gave a red gum which was treated in acetone with excess maleic acid to give 5-methyl-2-(4-[(-2-[2,2,2-trifluoroethyl]guanidino)thiazol-4-yl]butylamino)pyrimid-4-one containing 1.75 equivalents of maleic acid. The n.m.r. of this compound in d6 dimethylsulphoxide using tetramethylsilane as internal standard (δ=0) included the following resonances (δ):-1.6 (multiplet, 4H); 1.8 (singlet, 3H); 3.3 (multiplet, 2H); 4.2 (quartet, 2H); 6.6 (singlet, 1H); 7.5 (singlet, 1H).

Workup

  1. temperaturewas heated
  2. customThe mixture was then evaporated to dryness
  3. customthe residue purified by preparative thin layer chromatography
  4. extractionThe appropriate band was extracted with chloroform/ethanol 1:1 v/v (200 ml.)
  5. customEvaporation of the solvent to dryness
  6. customgave a red gum which

Sources & evidence

ORD record
ord-b1f94f047171423488c70c2fa536816a
Source dataset
uspto-grants-1982_12
Patent number
US04362728

Reaction notes

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