Sodium Phosphate, Monobasic, Monohydrate → 3-({2,4-Dimethyl-5-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}carbamoyl)-5-(pentafluoro-lambda6-sulphanyl)benzoic acid

HRID 1055754Notes

Reaction equation

HRID 1055754 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:16]3[N:12]([N:13]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[CH:11]=[CH:10]2)=[CH:4][C:3]=1[NH:23][C:24](=[O:39])[C:25]1[CH:30]=[C:29]([S:31]([F:36])([F:35])([F:34])([F:33])[F:32])[CH:28]=[C:27]([CH:37]=[O:38])[CH:26]=1.O.P([O-])(O)(O)=[O:42].[Na+].Cl([O-])=O.[Na+]>CS(C)=O.O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:16]3[N:12]([N:13]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[CH:11]=[CH:10]2)=[CH:4][C:3]=1[NH:23][C:24]([C:25]1[CH:26]=[C:27]([CH:28]=[C:29]([S:31]([F:35])([F:34])([F:33])([F:36])[F:32])[CH:30]=1)[C:37]([OH:42])=[O:38])=[O:39]

Participants

6

Reactant 3

HCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 86690986N-{2,4-Dimethyl-5-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-3-formyl-5-(penta-fluoro-lambda6-sulphanyl)benzamide

Product 1

HCID 866909853-({2,4-Dimethyl-5-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}carbamoyl)-5-(pentafluoro-lambda6-sulphanyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent3×

Procedure

100 mg (0.142 mmol, 80% pure) of the compound from Example 77A were dissolved in 2 ml of DMSO, and a solution of 48 mg (0.350 mmol) of sodium dihydrogenphosphate hydrate in 0.7 ml of water was added at RT. A solution of 39 mg (0.342 mmol) of sodium chlorite in 0.3 ml of water was then added dropwise. The reaction mixture was stirred at RT for 24 h and then diluted with 100 ml of water and extracted three times with in each case about 100 ml of ethyl acetate. The combined organic extracts were washed with saturated sodium chloride solution, dried over anhydrous magnesium sulphate, filtered and freed from the solvent on a rotary evaporator. The crude product obtained in this manner was purified by preparative HPLC (Method 32). After evaporation of the product fractions, the residue was stirred in a mixture of 2 ml of pentane, 0.5 ml of dichloromethane and 0.5 ml of diisopropyl ether for 10 min. Filtration with suction and drying of the solid under high vacuum gave 43 mg (52% of theory) of the title compound.

Workup

  1. extractionextracted three times with in each case about 100 ml of ethyl acetate
  2. washThe combined organic extracts were washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customfreed from the solvent on a rotary evaporator
  6. customThe crude product obtained in this manner
  7. customwas purified by preparative HPLC (Method 32)
  8. customAfter evaporation of the product fractions
  9. stirringthe residue was stirred in a mixture of 2 ml of pentane, 0.5 ml of dichloromethane and 0.5 ml of diisopropyl ether for 10 min
  10. filtrationFiltration with suction
  11. customdrying of the solid under high vacuum

Sources & evidence

ORD record
ord-530483bf3fd649f3adbbd517e7639e72
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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