1,4-Dioxane → 2-(4-Cyclohexylthiocarbamoyl-piperazin-1-yl)-4-amino-6,7-dimethoxyquinazoline

HRID 364886

Reaction equation

HRID 364886 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:9]([NH2:19])=[N:10][C:11]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[N:12][C:6]2=[CH:5][C:4]=1[O:20][CH3:21].[CH:22]1([N:27]=[C:28]=[S:29])[CH2:26][CH2:25][CH2:24][CH2:23]1.O1CCOC[CH2:31]1>>[CH:22]1([NH:27][C:28]([N:16]2[CH2:17][CH2:18][N:13]([C:11]3[N:10]=[C:9]([NH2:19])[C:7]4[C:6](=[CH:5][C:4]([O:20][CH3:21])=[C:3]([O:2][CH3:1])[CH:8]=4)[N:12]=3)[CH2:14][CH2:15]2)=[S:29])[CH2:31][CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 141792Cyclopentyl isothiocyanateHCID 6162672-(1-Piperazinyl)-4-amino-6,7-dimethoxyquinazoline

Product 1

HCID 137140982-(4-Cyclohexylthiocarbamoyl-piperazin-1-yl)-4-amino-6,7-dimethoxyquinazoline

Procedure

To a solution prepared by dissolving 868 mg. (3 mmole) of 2-piperazine-4-amino-6,7-dimethoxyquinazoline in 30 ml of dioxane, there was added dropwise 424 mg. (13 mmole) of cyclopentyl isothiocyanate at room temperature. The mixture was stirred overnight at room temperature. After evaporation of the solvent from the reaction mixture, the residue was chromatographed on silica gel, and eluted with 2% ethanol-chloroform to obtain 1.26 g. of the desired product. The product was dissolved in 10 ml of iso-propanol and 2 ml of 2N hydrochloric acid was added to the resultant solution to form a hydrochloride, which was in turn isolated.

Workup

  1. customTo a solution prepared
  2. dissolutionby dissolving 868 mg
  3. customat room temperature
  4. customAfter evaporation of the solvent from the reaction mixture
  5. customthe residue was chromatographed on silica gel
  6. washeluted with 2% ethanol-chloroform
  7. customto obtain 1.26 g

Sources & evidence

ORD record
ord-f06bd359ea864ba6a5b36344d25835d1
Source dataset
uspto-grants-1986_08
Patent number
US04607034

Linked notes

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