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

HRID 719291ノート

反応式

HRID 719291 の反応式
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

参加物

4

反応物 2

HCID 14812Phosphorus oxide (P4O10)HCID 178434580HCID 178434580、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-afb4d1f320ca495ca5f10c744ba44a48
出典データセット
uspto-grants-2006_11
特許番号
US07132428B2

反応ノート

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