1-Methylpiperazine → 3,5-Dimethyl-2-[4-[4-(4-methylpiperazinylmethyl)benzoyl]benzylthio]-4(3H)-quinazolinone

HRID 1291337Notes

Reaction equation

HRID 1291337 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:13])[N:4]=[C:3]1[SH:14].Br[CH2:16][C:17]1[CH:32]=[CH:31][C:20]([C:21]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29]Br)=[CH:25][CH:24]=2)=[O:22])=[CH:19][CH:18]=1.[CH3:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.[OH-].[Na+].O>CN(C=O)C>[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:13])[N:4]=[C:3]1[S:14][CH2:16][C:17]1[CH:32]=[CH:31][C:20]([C:21](=[O:22])[C:23]2[CH:28]=[CH:27][C:26]([CH2:29][N:37]3[CH2:38][CH2:39][N:34]([CH3:33])[CH2:35][CH2:36]3)=[CH:25][CH:24]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 23039244,4'-Bis(bromomethyl)benzophenoneHCID 23719242Sodium hydroxide--water (1/1/1)HCID 178424003HCID 178424003, compound

Product 1

HCID 189192153,5-Dimethyl-2-[4-[4-(4-methylpiperazinylmethyl)benzoyl]benzylthio]-4(3H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3,5-dimethyl-2-mercapto-4(3H)quinazolinone (1.03 g), 4,4'-bis (bromomethyl)benzophenone (1.75 g), N-methylpiperazine (500 ml) and 1N-sodium hydroxide/water (5.5 ml) in DMF (35 ml) was stirred at room temperature for 30 minutes. This reaction mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (chloroform: methanol: aqueous ammonia=40:1:0.1) to provide the title compound as colorless amorphous solid (180 mg).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (chloroform: methanol: aqueous ammonia=40:1:0.1)

Sources & evidence

ORD record
ord-fb53c5ba18e7453daecae87886e0d79c
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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