1-Methylpiperazine → 1-Cyclohexyl-5-[2-methoxy-4-(4-methyl-1-piperazinyl)phenyl]-3-methyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 915922노트

반응식

HRID 915922 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.Br[C:28]1[CH:33]=[CH:32][C:31]([C:34]2[NH:35][C:36](=[O:50])[C:37]3[N:42]([CH:43]4[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]4)[N:41]=[C:40]([CH3:49])[C:38]=3[N:39]=2)=[C:30]([O:51][CH3:52])[CH:29]=1>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH:43]1([N:42]2[C:37]3[C:36](=[O:50])[NH:35][C:34]([C:31]4[CH:32]=[CH:33][C:28]([N:5]5[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]5)=[CH:29][C:30]=4[O:51][CH3:52])=[N:39][C:38]=3[C:40]([CH3:49])=[N:41]2)[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1

참가 물질

8

반응물 4

HCID 531671-MethylpiperazineHCID 83681Tris(1,1-dimethylethyl)phosphine2회HCID 23676156Sodium t-butoxideHCID 136005882HCID 136005882, 화합물

생성물 1

HCID 1360057831-Cyclohexyl-5-[2-methoxy-4-(4-methyl-1-piperazinyl)phenyl]-3-methyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one수율 38%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매2회HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

In a stream of argon, 166 μl (1.50 mmol) of N-methylpiperazine, 72 mg (0.75 mmol) of sodium tert-butoxide, 166 mg (0.01 mmol) of tri-tert-butylphosphine, and 1.6 mg (0.008 mmol) of palladium(II) acetate were added to a 2 ml toluene solution of 209 mg (0.50 mmol) of the compound obtained in Example 15, and the mixture was stirred at 110° C. for 2 hours. Further, 166 mg (0.01 mmol) of tri-tert-butylphosphine and 1.6 mg (0.008 mmol) of palladium(II) acetate were added, and the mixture was stirred at 110° C. for 8 hours. Then, the reaction mixture was brought to room temperature, diluted with water, and then 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=20/1) to obtain 82 mg (38%) of the captioned compound.

후처리

  1. stirringthe mixture was stirred at 110° C. for 8 hours
  2. customwas brought to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform/methanol=20/1)

출처 및 근거

ORD 기록
ord-2640370e1df244eca668cd5b73958f91
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268128B2

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