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Tetrahydrofuran → 1-Cyclohexyl-5-[4-(4-hydroxy-1-methyl-4-piperidinyl)-2-methoxyphenyl]-3-methyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 915948
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인쇄 미리보기

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HRID 915948 반응식
C([Li])CCC.O1CCCC1.Br[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[NH:19][C:20](=[O:34])[C:21]3[N:26]([CH:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)[N:25]=[C:24]([CH3:33])[C:22]=3[N:23]=2)=[C:14]([O:35][CH3:36])[CH:13]=1.[CH3:37][N:38]1[CH2:43][CH2:42][C:41](=[O:44])[CH2:40][CH2:39]1>O>[CH:27]1([N:26]2[C:21]3[C:20](=[O:34])[NH:19][C:18]([C:15]4[CH:16]=[CH:17][C:12]([C:41]5([OH:44])[CH2:42][CH2:43][N:38]([CH3:37])[CH2:39][CH2:40]5)=[CH:13][C:14]=4[O:35][CH3:36])=[N:23][C:22]=3[C:24]([CH3:33])=[N:25]2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 740491-Methyl-4-piperidoneHCID 136005882HCID 136005882, 화합물HCID 178418339Butyllithium

생성물 1

HCID 1360059331-Cyclohexyl-5-[4-(4-hydroxy-1-methyl-4-piperidinyl)-2-methoxyphenyl]-3-methyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one수율 55.1%

시약·촉매·용매 1

HCID 962
Water
용매

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온도
-78 °C

실험 절차

In an atmosphere of argon, 0.95 ml of n-butyl lithium (1.59M/hexane solution, 1.51 mmol) was added dropwise at −78° C. to a 10 ml anhydrous tetrahydrofuran solution of 300 mg (0.72 mmol) of the compound obtained in Example 15. The mixture was stirred at −78° C. for 30 minutes, and then 133 μl (1.08 mmol) of 1-methyl-4-piperidone was added, followed by heating the mixture gradually to 0° C. over the course of 1 hour. Then, water was added to the reaction mixture, and then the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/1) to obtain 179 mg (55%) of the captioned compound.

후처리

  1. temperatureby heating the mixture gradually to 0° C. over the course of 1 hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=100/1)

출처 및 근거

ORD 기록
ord-0dccdb9d2a3b42118bb24c3baa76b994
출처 데이터셋
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07268128B2

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