Sodium Bicarbonate → 3-(2-methanesulfonyl-pyrimidin-4-yl)-1-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylic acid 2-chloro-benzylamide

HRID 1455253Notes

Reaction equation

HRID 1455253 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][NH:5][C:6]([C:8]1[C:15](=[O:16])[N:11]2[CH2:12][CH2:13][CH2:14][N:10]2[C:9]=1[C:17]1[CH:22]=[CH:21][N:20]=[C:19](SC)[N:18]=1)=[O:7].O[O:30][S:31]([O-:33])=O.[K+].S([O-])(O[O-])(=O)=O.[K+].[K+].[C:43]([O-])(O)=O.[Na+]>C1COCC1.CO.O>[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][NH:5][C:6]([C:8]1[C:15](=[O:16])[N:11]2[CH2:12][CH2:13][CH2:14][N:10]2[C:9]=1[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([S:31]([CH3:43])(=[O:33])=[O:30])[N:18]=1)=[O:7]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 10313463Potassium peroxymonosulphateHCID 23707502Potassium hydroxy sulfiteHCID 575317953-(2-methylsulfanyl-pyrimidin-4-yl)-1-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylic acid 2-chloro-benzylamide

Product 1

HCID 575317923-(2-methanesulfonyl-pyrimidin-4-yl)-1-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylic acid 2-chloro-benzylamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 3-(2-methylsulfanyl-pyrimidin-4-yl)-1-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylic acid 2-chloro-benzylamide, 15, (0.20 g, 0.48 mmol) in THF/MeOH (8 mL of 1:1 mixture) was added dropwise a solution of Oxone® (potassium peroxymonosulfate) (in H2O (8 mL). After stirring the reaction for 1.5 h at room temperature, the solution was poured into aqueous saturated NaHCO3. The aqueous phase is extracted with CHCl3 (×3). The combined organic phases are dried (MgSO4), filtered and concentrated in vacuo to afford the desired product which is used without further purification.

Workup

  1. customthe reaction for 1.5 h at room temperature
  2. extractionThe aqueous phase is extracted with CHCl3 (×3)
  3. dry with materialThe combined organic phases are dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b76ff70fa1d453f9656604b7507b82d
Source dataset
uspto-grants-2009_01
Patent number
US07482356B2

Reaction notes

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