Methanesulfonic anhydride → HCID 59867808, compound

HRID 1662706Notes

Reaction equation

HRID 1662706 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10](O)([C:11]3[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=3[O:18][CH3:19])[C:9](=[O:21])[N:8]([S:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=3[O:33][C:34]([F:37])([F:36])[F:35])(=[O:24])=[O:23])[C:5]2=[N:6][CH:7]=1.CS(OS(C)(=O)=O)(=O)=O.FC(F)(F)C(O)=O.[OH:54][C@H:55]1[CH2:59][NH:58][C@H:57]([C:60]([N:62]([CH3:64])[CH3:63])=[O:61])[CH2:56]1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CCN(CC)CC>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([N:58]3[CH2:59][C@H:55]([OH:54])[CH2:56][C@H:57]3[C:60]([N:62]([CH3:64])[CH3:63])=[O:61])([C:11]3[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=3[O:18][CH3:19])[C:9](=[O:21])[N:8]([S:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=3[O:33][C:34]([F:35])([F:36])[F:37])(=[O:24])=[O:23])[C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 81560Methanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 674277675-bromo-3-hydroxy-3-(2-methoxy-5-methylphenyl)-1-{[4-methoxy-2-(trifluoromethoxy)phenyl]sulfonyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-oneHCID 67429482(4R)-4-hydroxy-N,N-dimethyl-L-prolinamide trifluoroacetate

Product 1

HCID 59867808HCID 59867808, compoundYield 1.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent2×

Procedure

To a solution of 290 mg of the compound obtained in Step 120-5 and 97 mg of Et3N in CHCl3 (2 ml), on ice, was added 101 mg of methanesulfonic acid anhydride and the reaction mixture was stirred at room temperature for one hour. The solution was cooled again under ice cooling, 97 mg of Et3N and 261 mg of (4R)-4-hydroxy-N,N-dimethyl-L-prolinamide trifluoroacetate was added, and the reaction mixture was stirred at room temperature for two hours. A saturated aqueous solution of NaHCO3 was poured, and the solution was extracted with EtOAc. The organic layer was washed with saturated brine, dried over Na2SO4, then, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. The obtained residue was purified by thin layer chromatography (silicagel 60 F254; 1 mm thick; mobile phase: CHCl3/MeOH=9/1; v/v) to obtain 6 mg of the title compound (amorphous).

Workup

  1. temperatureThe solution was cooled again under ice cooling
  2. stirringthe reaction mixture was stirred at room temperature for two hours
  3. extractionthe solution was extracted with EtOAc
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over Na2SO4
  6. customthe drying agent was separated by filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by thin layer chromatography (silicagel 60 F254; 1 mm thick; mobile phase: CHCl3/MeOH=9/1; v/v)

Sources & evidence

ORD record
ord-3fc2f732e38d458087fdd1d746c2f35f
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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