Potassium caroate → 3-(4-Methoxybenzyl)-9-(methylsulfonyl)-6,7-dihydro-3h-pyrazolo[4',3':5,6]pyrido[4,3-f]quinazoline

HRID 2383408Notes

Reaction equation

HRID 2383408 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:24][CH2:23][C:22]5[N:21]=[C:20](SC)[N:19]=[CH:18][C:17]=5[C:16]=4[C:11]=3[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[OH:29][S:30]([O-:33])(=O)=O.OS(O[O-])(=O)=O.OS(O[O-])(=O)=O.[O-]S([O-])(=O)=O.[K+].[K+].[K+].[K+].[K+].[CH3:56]O.O>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:24][CH2:23][C:22]5[N:21]=[C:20]([S:30]([CH3:56])(=[O:33])=[O:29])[N:19]=[CH:18][C:17]=5[C:16]=4[C:11]=3[CH:10]=[N:9]2)=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 15793144Potassium caroateHCID 22242641Methanol--water (1/1)HCID 594904193-(4-methoxybenzyl)-9-(methylsulfanyl)-6,7-dihydro-3H-pyrazolo[4',3':5,6]pyrido[4,3-f]quinazoline

Product 1

HCID 594904633-(4-Methoxybenzyl)-9-(methylsulfonyl)-6,7-dihydro-3h-pyrazolo[4',3':5,6]pyrido[4,3-f]quinazolineYield 77%

Procedure

To a suspension of 3-(4-methoxybenzyl)-9-(methylsulfanyl)-6,7-dihydro-3H-pyrazolo[4′,3′:5,6]pyrido[4,3-f]quinazoline (1.9 g, 4.8 mmol) in 2:1 mixture of methanol-water (100 mL) was added potassium monopersulfate triple salt (Oxone®, 9.2 g, 15 mmol) and the suspension stirred for 18 hours. On completion of the reaction, the mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (200 mL) and washed with water (2×20 mL), dried using anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the desired product, 3-(4-methoxybenzyl)-9-(methylsulfonyl)-6,7-dihydro-3H-pyrazolo[4′,3′:5,6]pyrido[4,3-f]quinazoline (1.5 g, 77%) as a tan solid. LCMS [M+H]: 422. The compound was used without any further purification.

Workup

  1. customOn completion of the reaction
  2. concentrationthe mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  4. washwashed with water (2×20 mL)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-08dd2d0d8bb64b818a30a80b5929cb9f
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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