Triethylamine → 2-[4-(4-Isopropylcinnamoyl)-piperazin-1-yl]-4-amino-6,7-dimethoxyquinazolin

HRID 1449159Notes

Reaction equation

HRID 1449159 reaction equation
[CH:1]([C:4]1[CH:14]=[CH:13][C:7]([CH:8]=[CH:9][C:10]([OH:12])=O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)OCC.Cl.[N:29]1([C:35]2[N:44]=[C:43]([NH2:45])[C:42]3[C:37](=[CH:38][C:39]([O:48][CH3:49])=[C:40]([O:46][CH3:47])[CH:41]=3)[N:36]=2)[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>CC(C)=O>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[CH:9][C:10]([N:32]2[CH2:33][CH2:34][N:29]([C:35]3[N:44]=[C:43]([NH2:45])[C:42]4[C:37](=[CH:38][C:39]([O:48][CH3:49])=[C:40]([O:46][CH3:47])[CH:41]=4)[N:36]=3)[CH2:30][CH2:31]2)=[O:12])=[CH:13][CH:14]=1)([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 728543-(4-(1-Methylethyl)phenyl)-2-propenoic acidHCID 204738332-Piperazine-4-amino-6,7-dimethoxyquinazoline hydrochloride

Product 1

HCID 544068222-[4-(4-Isopropylcinnamoyl)-piperazin-1-yl]-4-amino-6,7-dimethoxyquinazolin

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 342 mg. of 4-isopropylcinnamic acid and 727 mg. of triethylamine in 20 ml. of acetone were added dropwise under ice-cooling 195 mg. of ethyl chlorocarbonate and the resulting mixture was stirred for 3.5 hours. Then, 543 mg. of 2-(piperazin-1-yl)-4-amino-6,7-dimethoxyquinazoline.hydrochloride were added thereto and stirring was continued at room temperature overnight. Then, the acetone was distilled off, the residue was dissolved in 20 ml. of 10% K2CO3 and extracted with ethyl acetate. After drying over magnesium sulfate, the extract was concentrated and recrystallization from methanol gave 361 mg. of the desired product.

Workup

  1. additionTo a mixture of 342 mg
  2. temperaturecooling 195 mg
  3. distillationThen, the acetone was distilled off
  4. dissolutionthe residue was dissolved in 20 ml
  5. extractionof 10% K2CO3 and extracted with ethyl acetate
  6. dry with materialAfter drying over magnesium sulfate
  7. concentrationthe extract was concentrated
  8. customrecrystallization from methanol
  9. customgave 361 mg

Sources & evidence

ORD record
ord-11cb611237c5439e89410348931acdb0
Source dataset
uspto-grants-1980_02
Patent number
US04189484

Reaction notes

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