Ethylene Glycol → 2-methyl-3-[2-[4-(1-phenyl-1H-indazol-3-yl)-1-piperazinyl]ethyl]-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 2051021Notes

Reaction equation

HRID 2051021 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[N:29][NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]2[C:22](=[O:23])[N:21]3[CH:24]=[CH:25][CH:26]=[CH:27][C:20]3=[N:19][C:18]=2[CH3:28])[CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+].C(O)CO>O>[CH3:28][C:18]1[N:19]=[C:20]2[CH:27]=[CH:26][CH:25]=[CH:24][N:21]2[C:22](=[O:23])[C:17]=1[CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][N:9]([C:8]2[C:3]3[C:4](=[CH:5][CH:6]=[CH:7][CH:2]=3)[N:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[N:29]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 11430Potassium CarbonateHCID 566196993-[2-[4-[(2-fluorophenyl)(2-phenylhydrazono)methyl]-1-piperazinyl]ethyl]-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Product 1

HCID 151705162-methyl-3-[2-[4-(1-phenyl-1H-indazol-3-yl)-1-piperazinyl]ethyl]-4H-pyrido[1,2-a]pyrimidin-4-oneYield 25.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.5 parts of 3-[2-[4-[(2-fluorophenyl)(2-phenylhydrazono)methyl]-1-piperazinyl]ethyl]-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, 1 part of potassium carbonate and 27.8 parts of 1,2-ethanediol was stirred overnight at reflux temperature. The reaction mixture was cooled and then poured into water. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in 2-propanol. The salt was filtered off and dried, yielding 0.7 parts (25.5%) of 2-methyl-3-[2-[4-(1-phenyl-1H-indazol-3-yl)-1-piperazinyl]ethyl]-4H-pyrido[1,2-a]pyrimidin-4-one; mp. 260.0° C. (decomp.) (compound 4).

Workup

  1. temperatureat reflux temperature
  2. temperatureThe reaction mixture was cooled
  3. extractionThe product was extracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. filtrationThe salt was filtered off
  12. customdried

Sources & evidence

ORD record
ord-5fdd8d3f1fd04ef3b130f91faec7b3a2
Source dataset
uspto-grants-1991_05
Patent number
US05015740

Reaction notes

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