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Piperidine → Piperiacetildenafil

HRID 1532092
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HRID 1532092 반응식
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]([O:31][CH2:32][CH3:33])=[C:15]([C:17]2[NH:18][C:19](=[O:30])[C:20]3[N:25]([CH3:26])[N:24]=[C:23]([CH2:27][CH2:28][CH3:29])[C:21]=3[N:22]=2)[CH:16]=1)=[O:10].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:32]([O:31][C:14]1[CH:13]=[CH:12][C:11]([C:9](=[O:10])[CH2:8][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:16][C:15]=1[C:17]1[NH:18][C:19](=[O:30])[C:20]2[N:25]([CH3:26])[N:24]=[C:23]([CH2:27][CH2:28][CH3:29])[C:21]=2[N:22]=1)[CH3:33]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 1357385501,4-Dihydro-5-[5-bromoacetyl)-2-ethoxyphenyl]-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one

생성물 1

HCID 135564757Piperiacetildenafil수율 28%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Piperidine (0.22 ml, 0.0022 mol) was added to a stirred suspension of 5-(5-bromoacetyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (Preparation 8, 0.95 g, 0.0022 mol) and anhydrous potassium carbonate (0.6 g, 0.0044 mol) in acetonitrile (50 ml) at room temperature. After 18 hours the mixture was evaporated under vacuum, the residue dissolved in water (50 ml) and the solution extracted with ethyl acetate (3×30 ml). The organic extracts were combined, washed with brine (3×20 ml), dried (Na2SO4) and evaporated under vacuum. The resulting yellow solid was chromatographed on silica gel (12 g), using a methanol in dichloromethane elution gradient (0-2% methanol), to give an off-white solid. Crystallisation from ethyl acetate-hexane gave the title compound as an off-white powder (0.27 g, 28%), m.p. 149-151° C. Found: C,66.13; H,6.90; N, 15.95. C24H31N5O5 requires C,65.88; H,7.14; N,16.01%.

후처리

  1. customAfter 18 hours the mixture was evaporated under vacuum
  2. dissolutionthe residue dissolved in water (50 ml)
  3. extractionthe solution extracted with ethyl acetate (3×30 ml)
  4. washwashed with brine (3×20 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under vacuum
  7. customThe resulting yellow solid was chromatographed on silica gel (12 g)
  8. washa methanol in dichloromethane elution gradient (0-2% methanol)
  9. customto give an off-white solid
  10. customCrystallisation from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-82ad2fd953484ad2b668cf9f95fff9d3
출처 데이터셋
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06200980B1

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