Phosphorus oxide (P4O10) → 1-Benzyl-5-cyclohexyl-3-methyl-1H-pyrazolo[4,3-c]isoquinoline

HRID 719291노트

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HRID 719291 반응식
CC1C(NC(C2SC=CC=2)=O)=C(C2C=CC=CC=2)NN=1.[CH2:21]([N:28]1[C:32]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:31]([NH:39][C:40]([CH:42]2[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)=O)[C:30]([CH3:48])=[N:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>P(Cl)(Cl)(Cl)=O>[CH2:21]([N:28]1[C:32]2[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[C:40]([CH:42]3[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]3)=[N:39][C:31]=2[C:30]([CH3:48])=[N:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

4

반응물 2

HCID 14812Phosphorus oxide (P4O10)HCID 178434580HCID 178434580, 화합물

생성물 1

HCID 113142591-Benzyl-5-cyclohexyl-3-methyl-1H-pyrazolo[4,3-c]isoquinoline

시약·촉매·용매 1

HCID 24813Phosphorus oxychloride용매

반응 조건

온도
120 °C

실험 절차

To a suspension of 462 mg of cyclohexanecarboxylic acid (1-benzyl-3-methyl-5-phenyl-1H-pyrazol-4-yl)-amide thiophene-2-carboxylic acid (3-methyl-5-phenyl-1H-pyrazol-4-yl)-amide in 5.6 mL of phosphorous oxychloride was added 2.57 g of phosphorous pentoxide and the resulting suspension was heated at 120° C. for 5 h. The reaction mixture was cooled to rt and quenched with the addition of ice and water and then neutralized with solid sodium carbonate. The aqueous mixture was extracted with ethyl acetate and the combined organic extracts were washed with brine, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was purified by means of MPLC (12 g SiO2, 40% EtOAc:Heptane) to give the title compound as a tan solid.

후처리

  1. temperatureThe reaction mixture was cooled to rt
  2. customquenched with the addition of ice and water
  3. extractionThe aqueous mixture was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by means of MPLC (12 g SiO2, 40% EtOAc:Heptane)

출처 및 근거

ORD 기록
ord-afb4d1f320ca495ca5f10c744ba44a48
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132428B2

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