2-(1-Piperazinyl)-4-amino-6,7-dimethoxyquinazoline → 4-Amino-6,7-dimethoxy-2-[4-(isoxazole-3-carbonyl)-piperazin-1-yl]quinazoline Hydrochloride

HRID 1384936Notes

Reaction equation

HRID 1384936 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([Cl:8])=[O:7])=[N:2]1.[NH2:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[C:12]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[N:11]=1>O1CCOCC1>[ClH:8].[NH2:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[C:12]([N:24]2[CH2:29][CH2:28][N:27]([C:6]([C:3]3[CH:4]=[CH:5][O:1][N:2]=3)=[O:7])[CH2:26][CH2:25]2)[N:11]=1

Participants

4

Reactant 2

HCID 6162672-(1-Piperazinyl)-4-amino-6,7-dimethoxyquinazolineHCID 110079401,2-Oxazole-3-carbonyl chloride

Product 1

HCID 211840254-Amino-6,7-dimethoxy-2-[4-(isoxazole-3-carbonyl)-piperazin-1-yl]quinazoline Hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of isoxazole-3-carbonyl chloride (0.753 g., 0.0057 mole) in dioxane (20 ml.) was added to a solution of 4-amino-6,7-dimethoxy-2-(1-piperazinyl)quinazoline (1.66 g., 0.0057 mole) in dioxane (60 ml.). The mixture was stirred at reflux for 30 minutes, then at room temperature for 64 hours. Filtration gave the title compound which was recrystallized from methanol (1.81 g., 75% yield). The product had a m.p. of 268°-273° C. with decomposition.

Workup

  1. temperatureat reflux for 30 minutes
  2. filtrationFiltration

Sources & evidence

ORD record
ord-b24504e2d26b4273b781a4304a7eb3fd
Source dataset
uspto-grants-2001_07
Patent number
US06262059B1

Reaction notes

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