(+/-)-ethyl 4-[5-[2-[1-(4-chlorobenzoyl)propyl]-2,3-dihydro-3-oxo-4H-1,2,4-triazol-4-yl]-2-pyridinyl]-1-piperazinecarboxylate → (+/-)-2-[1-(4-chlorobenzoyl) propyl]2,4-dihydro-4-[6-(1-piperazinyl)-3-pyridinyl]-3H-1,2,4-triazol-3-one monohydrochloride

HRID 2092

反応式

HRID 2092 の反応式
[Cl:1][C:2]1[CH:35]=[CH:34][C:5]([C:6]([CH:8]([N:11]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[CH:19][C:20]([N:23]4[CH2:28][CH2:27][N:26](C(OCC)=O)[CH2:25][CH2:24]4)=[N:21][CH:22]=3)[CH:13]=[N:12]2)[CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1>Br.O>[ClH:1].[Cl:1][C:2]1[CH:35]=[CH:34][C:5]([C:6]([CH:8]([N:11]2[C:15](=[O:16])[N:14]([C:17]3[CH:22]=[N:21][C:20]([N:23]4[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]4)=[CH:19][CH:18]=3)[CH:13]=[N:12]2)[CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1

参加物

4

反応物 1

HCID 53958409(+/-)-ethyl 4-[5-[2-[1-(4-chlorobenzoyl)propyl]-2,3-dihydro-3-oxo-4H-1,2,4-triazol-4-yl]-2-pyridinyl]-1-piperazinecarboxylate

生成物 1

HCID 18972843(+/-)-2-[1-(4-chlorobenzoyl) propyl]2,4-dihydro-4-[6-(1-piperazinyl)-3-pyridinyl]-3H-1,2,4-triazol-3-one monohydrochloride収率 39.4%

試薬・触媒・溶媒 2

HCID 260Hydrogen Bromide溶媒HCID 962Water溶媒

実験手順

A mixture of (±)-ethyl 4-[5-[2-[1-(4-chlorobenzoyl)propyl]-2,3-dihydro-3-oxo-4H-1,2,4-triazol-4-yl]-2-pyridinyl]-1-piperazinecarboxylate (24 g) in hydrobromic acid, 48% solution in water (250 ml) was stirred and refluxed overnight. The solvent was evaporated and the residue was dissolved in CH2Cl2, neutralized with NH4OH/H2O and extracted with CH2 Cl2. The organic layer was washed with water, dried, filtered and evaporated. A sample (3.5 g) of the residue (total 18 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 99/1). The pure fractions were collected and evaporated. The residue was dissolved in 2-propanol and crystallized into the hydrochloric acid salt (1:1) in 2-propanol. The precipitate was filtered off, washed with 2-propanol and dried at 150° C. The product was dissolved in 2-propanol. Pyridine was added dropwise until all the product was dissolved and subsequently crystallized. The precipitate was filtered off and dried, yielding 1.7 g (±)-2-[1-(4-chlorobenzoyl)propyl]-2,4-dihydro-4-[6-(1-piperazinyl)-3-pyridinyl]-3H-1,2,4-triazol-3-one monohydrochloride (39.4%); mp. 209.8° C. (interm. 1).

後処理

  1. temperaturerefluxed overnight
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in CH2Cl2
  4. extractionextracted with CH2 Cl2
  5. washThe organic layer was washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customA sample (3.5 g) of the residue (total 18 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 99/1)
  10. customThe pure fractions were collected
  11. customevaporated
  12. dissolutionThe residue was dissolved in 2-propanol
  13. customcrystallized into the hydrochloric acid salt (1:1) in 2-propanol
  14. filtrationThe precipitate was filtered off
  15. washwashed with 2-propanol
  16. customdried at 150° C
  17. dissolutionThe product was dissolved in 2-propanol
  18. additionPyridine was added dropwise until all the product
  19. dissolutionwas dissolved
  20. customsubsequently crystallized
  21. filtrationThe precipitate was filtered off
  22. customdried

出典と根拠

ORDレコード
ord-3f4808599fe74e18a7bf471d2d4e9057
出典データセット
uspto-grants-1998_03
特許番号
US05728700

関連ノート

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