4-(Chloromethyl)phenyl isocyanate → N-[4-(chloromethyl)phenyl]-4-(6,7-dimethoxy-4-quinazolinyl)-1-piperazinecarboxamide

HRID 353127Notes

Reaction equation

HRID 353127 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.[Cl:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]=[C:30]=[O:31])=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[Cl:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([N:18]2[CH2:17][CH2:16][N:15]([C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][N:7]=3)[CH2:20][CH2:19]2)=[O:31])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 27333194-(Chloromethyl)phenyl isocyanateHCID 27584846,7-Dimethoxy-4-piperazin-1-yl-quinazoline

Product 1

HCID 22707657N-[4-(chloromethyl)phenyl]-4-(6,7-dimethoxy-4-quinazolinyl)-1-piperazinecarboxamideYield 96.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 10 ml of toluene was suspended 593.5 mg (2.16 mmol) of 6,7-dimethoxy-4-piperazinylquinazoline obtained by the method described in South African Patent No. 67 06512 (1968), and 362.6 ml (2.16 mmol) of 4-(chloromethyl)phenyl isocyanate was added thereto, followed by stirring at room temperature for 3 hours. After the reaction mixture was filtered, the obtained crystals were washed with diisopropyl ether and dried under reduced pressure to give 916.8 mg (2.08 mmol, 96%) of N-[4-(chloromethyl)phenyl]-4-(6,7-dimethoxy-4-quinazolinyl)-1-piperazinecarboxamide. In 10 ml of dimethylformamide was dissolved 422.9 mg (0.96 mmol) of the obtained N-[4-(chloromethyl)phenyl]-4-(6,7-dimethoxy-4-quinazolinyl)-1-piperazinecarboxamide, and 0.28 ml (2.83 mmol) of piperidine was added thereto, followed by stirring at room temperature for 7 hours. Then, the reaction mixture was poured into water and the precipitated crystals were collected by filtration, followed by purification by silica gel column chromatography to give 430.9 mg (0.88 mmol) of the desired compound as colorless crystals.

Workup

  1. customobtained by the method
  2. filtrationAfter the reaction mixture was filtered
  3. washthe obtained crystals were washed with diisopropyl ether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-41064e09890047d5955aa73b6faae359
Source dataset
uspto-grants-2004_06
Patent number
US06750218B2

Reaction notes

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