Potassium Carbonate → 3-Methyl-2-[4-[6-(4-piperidinopiperidino)nicotinoyl]benzylthio]-4H-pyrido[1,2-a]pyrimidin-4-one trihydrochloride

HRID 1291390Notes

Reaction equation

HRID 1291390 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([C:8]2[CH:27]=[CH:26][C:11]([CH2:12][S:13][C:14]3[N:15]=[C:16]4[CH:25]=[CH:24][CH:23]=[CH:22][N:17]4[C:18](=[O:21])[C:19]=3[CH3:20])=[CH:10][CH:9]=2)=[O:7])=[CH:4][N:3]=1.[N:30]1([CH:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[ClH:1].[ClH:1].[ClH:1].[CH3:20][C:19]1[C:18](=[O:21])[N:17]2[CH:22]=[CH:23][CH:24]=[CH:25][C:16]2=[N:15][C:14]=1[S:13][CH2:12][C:11]1[CH:26]=[CH:27][C:8]([C:6](=[O:7])[C:5]2[CH:28]=[CH:29][C:2]([N:39]3[CH2:40][CH2:41][CH:36]([N:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)[CH2:37][CH2:38]3)=[N:3][CH:4]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 786071,4'-BipiperidineHCID 189190212-[4-(6-Chloronicotinoyl]benzylthio]-3-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Product 1

HCID 189189983-Methyl-2-[4-[6-(4-piperidinopiperidino)nicotinoyl]benzylthio]-4H-pyrido[1,2-a]pyrimidin-4-one trihydrochlorideYield 18.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[4-(6-chloronicotinoyl)benzylthio]-3-methyl-4H-pyrido[1,2-a]-pyrimidin-4-one (287 mg), 4-piperidinopiperidine (137 mg) and potassium carbonate (194 mg) in DMF (10 ml) was stirred at 80° C. for 24 hours. This reaction mixture was concentrated and the residue was dissolved in chloroform. The solution was washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (chloroform-methanol =9:1) and treated with hydrogen chloride/ethyl acetate to provide the title compound as colorless solid (28 mg).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in chloroform
  3. washThe solution was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (chloroform-methanol =9:1)
  7. additiontreated with hydrogen chloride/ethyl acetate

Sources & evidence

ORD record
ord-07e5dac7407b4e19b143ddc6d00b9848
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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