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

HRID 719291Notes

Reaction equation

HRID 719291 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
120 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-afb4d1f320ca495ca5f10c744ba44a48
Source dataset
uspto-grants-2006_11
Patent number
US07132428B2

Reaction notes

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