Cyclohexylthiourea → 7-[2-(Cyclohexylamino)-1,3-thiazol-5-yl]quinazolin-4(3h)-one

HRID 23357

Reaction equation

HRID 23357 reaction equation
Br[CH:2]([C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:15])[NH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1)[CH:3]=O.[CH:16]1([NH:22][C:23]([NH2:25])=[S:24])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CN(C)C=O>[CH:16]1([NH:22][C:23]2[S:24][C:2]([C:5]3[CH:14]=[C:13]4[C:8]([C:9](=[O:15])[NH:10][CH:11]=[N:12]4)=[CH:7][CH:6]=3)=[CH:3][N:25]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 1471603CyclohexylthioureaHCID 135531132Bromo-(4-oxo-3,4-dihydro-quinazolin-7-yl)acetaldehyde

Product 1

HCID 1354961657-[2-(Cyclohexylamino)-1,3-thiazol-5-yl]quinazolin-4(3h)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of bromo-(4-oxo-3,4-dihydro-quinazolin-7-yl)acetaldehyde and N-cyclohexylthiourea in dimethylformamide is heated at 70° C. until completion of the reaction (5-12 hours). The mixture is quenched with 10% dimethylamine in ethanol and the solvent is removed under reduced pressured. The crude is purified by chromatography on silica gel to isolate the desired compound.

Workup

  1. customThe mixture is quenched with 10% dimethylamine in ethanol
  2. customthe solvent is removed
  3. customThe crude is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-25238562fd52496693cf85f9c426924f
Source dataset
uspto-grants-2005_02
Patent number
US06852720B2

Linked notes

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