Potassium Carbonate → HCID 18919012, compound

HRID 1291383Notes

Reaction equation

HRID 1291383 reaction equation
[OH:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([C:8]2[CH:28]=[CH:27][C:11]([CH2:12][S:13][C:14]3[N:23]([CH3:24])[C:22](=[O:25])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][C:20]=4[CH3:26])[N:15]=3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.Cl.[Cl:32][CH2:33][C:34]1[CH:48]=[CH:47][C:37]([C:38]([N:40]2[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]2)=[O:39])=[CH:36][CH:35]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[ClH:32].[CH3:24][N:23]1[C:22](=[O:25])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[CH3:26])[N:15]=[C:14]1[S:13][CH2:12][C:11]1[CH:27]=[CH:28][C:8]([C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:33][C:34]3[CH:48]=[CH:47][C:37]([C:38]([N:40]4[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]4)=[O:39])=[CH:36][CH:35]=3)=[CH:30][CH:29]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 189188882-[4-(4-hydroxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinoneHCID 18919199HCID 18919199, compound

Product 1

HCID 18919012HCID 18919012, compoundYield 13.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[4-(4-hydroxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone (406 mg), 1-(4-chloromethylbenzoyl)-4-methylpiperazine hydrochloride (1.119 g) and potassium carbonate (739 mg) in DMF (10 ml) was stirred at room temperature for 40 hours. This reaction mixture was concentrated and the residue was purified by silica gel column chromatography (dichloromethane: methanol =9:1) and treated with hydrogen chloride/ethyl acetate to provide the title compound as colorless solid (86 mg).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (dichloromethane: methanol =9:1)
  3. additiontreated with hydrogen chloride/ethyl acetate

Sources & evidence

ORD record
ord-ca180bc097f0408da1cb21a947e95963
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…