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Acetic Acid → 5-Methyl-7-phenyl-2-[4-(phenylmethyl)-1-piperazinyl]-pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 482874
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HRID 482874 반응식
[C:1]1([C:7](=O)[CH2:8][C:9](=O)[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:13][C:14]1[C:18]([C:19]#[N:20])=[C:17]([N:21]2[CH2:26][CH2:25][N:24]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:23][CH2:22]2)[NH:16][N:15]=1.C(O)(=O)C>ClCCl>[CH3:10][C:9]1[CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:15]2[N:16]=[C:17]([N:21]3[CH2:26][CH2:25][N:24]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:23][CH2:22]3)[C:18]([C:19]#[N:20])=[C:14]2[N:13]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 7166BenzoylacetoneHCID 1785104933-Amino-5-(4-benzyl-1-piperazinyl)-4-pyrazolecarbonitrile

생성물 1

HCID 135799875-Methyl-7-phenyl-2-[4-(phenylmethyl)-1-piperazinyl]-pyrazolo[1,5-a]pyrimidine-3-carbonitrile수율 74.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 2.9 g (0.018 moles) of 1-phenyl-1,3-butanedione, 5.0 g (0.018 moles) of 3-amino-5-(4-phenylmethyl-1-piperazinyl)-4-pyrazolecarbonitrile (prepared as described in Example 1) and 25 ml of glacial acetic acid was refluxed for 4 hours. The reaction mixture was evaporated in vacuo and gave a thick oil. The oil was dissolved in dichloromethane and partitioned with saturated sodium bicarbonate. The organic layer was separated, dried over anhydrous sodium sulfate and passed through magnesium silicate. The solution was evaporated in vacuo and gave a yellow solid which was recrystallized from isopropanol and cyclohexane and gave 5.5 g of the desired product as a light yellow solid, mp 160°-164° C.

후처리

  1. temperaturewas refluxed for 4 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. customgave a thick oil
  4. custompartitioned with saturated sodium bicarbonate
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solution was evaporated in vacuo
  8. customgave a yellow solid which
  9. customwas recrystallized from isopropanol and cyclohexane

출처 및 근거

ORD 기록
ord-d2dbf030d2e94fa3be2b996bab2f0035
출처 데이터셋
uspto-grants-1986_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04576943

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