Betahistine → 3,5-Dimethyl-2-[4-[4-[2-[N-[2-(2-pyridyl)ethyl]-N-methylamino]ethoxy]benzoyl]benzylthio]-4(3H)-quinazolinone dihydrochloride

HRID 1291382Notes

Reaction equation

HRID 1291382 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:33]=[CH:32][C:8]([C:9]([C:11]2[CH:31]=[CH:30][C:14]([CH2:15][S:16][C:17]3[N:26]([CH3:27])[C:25](=[O:28])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][C:23]=4[CH3:29])[N:18]=3)=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1.[CH3:34][NH:35][CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=1.C(N(CC)CC)C>CN(C=O)C>[ClH:1].[ClH:1].[CH3:27][N:26]1[C:25](=[O:28])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][C:23]=2[CH3:29])[N:18]=[C:17]1[S:16][CH2:15][C:14]1[CH:30]=[CH:31][C:11]([C:9](=[O:10])[C:8]2[CH:32]=[CH:33][C:5]([O:4][CH2:3][CH2:2][N:35]([CH2:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=3)[CH3:34])=[CH:6][CH:7]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 2366BetahistineHCID 8471TriethylamineHCID 189188132-[4-[4-(2-Chloroethoxy)benzoyl]benzylthio]-3,5-dimethyl-4(3H)-quinazolinone

Product 1

HCID 189189763,5-Dimethyl-2-[4-[4-[2-[N-[2-(2-pyridyl)ethyl]-N-methylamino]ethoxy]benzoyl]benzylthio]-4(3H)-quinazolinone dihydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[4-[4-(2-chloroethoxy)benzoyl]-benzylthio]-3,5-dimethyl-4(3H)-quinazolinone (381 mg), 2-(2-methylaminoethyl)pyridine (0.17 ml) and triethylamine (0.33 ml) in DMF (7 ml) was stirred at 100° C. for 21 hours. This reaction mixture was concentrated and the residue was purified by silica gel column chromatography (dichloromethane: methanol: aqueous ammonia =9:1:0.1) and treated with hydrogen chloride/ethyl acetate to provide the title compound as colorless solid (256 mg).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (dichloromethane: methanol: aqueous ammonia =9:1:0.1)
  3. additiontreated with hydrogen chloride/ethyl acetate

Sources & evidence

ORD record
ord-2c726a10729f4c92a997ed35bbefd0cf
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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