Citric Acid → HCID 19083157, compound

HRID 1378928Notes

Reaction equation

HRID 1378928 reaction equation
[H-].[Na+].[CH:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.F[C:9]1[C:10]2[C:14]([CH:15]=[CH:16][CH:17]=1)=[N:13][N:12]([CH3:18])[C:11]=2[S:19]([NH2:22])(=[O:21])=[O:20].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O>[CH:3]1([CH2:6][O:7][C:9]2[C:10]3[C:14]([CH:15]=[CH:16][CH:17]=2)=[N:13][N:12]([CH3:18])[C:11]=3[S:19]([NH2:22])(=[O:21])=[O:20])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 190831614-fluoro-2-methyl-2H-indazole-3-sulfonamide

Product 1

HCID 19083157HCID 19083157, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.8 g (70 mmol) of 60% sodium hydride was suspended in 50 ml of DMSO, and 6 g (83 mmol) of cyclopropane methanol was dropwise added thereto. The mixture was stirred at room temperature for one hour, and then 5.4 g (24 mmol) of 4-fluoro-2-methyl-2H-indazole-3-sulfonamide was added thereto. The mixture was stirred at 130° C. for 3 hours. After the reaction, the mixture was poured into ice water, acidified with citric acid and extracted with ethyl acetate. The organic layer was washed with water and then concentrated. Formed crystals were collected by filtration, washed with IPE and then dried to obtain 5.8 g (yield: 90%) of the desired product. Melting point: 139°-141° C.

Workup

  1. stirringThe mixture was stirred at 130° C. for 3 hours
  2. customAfter the reaction
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. concentrationconcentrated
  6. customFormed crystals
  7. filtrationwere collected by filtration
  8. washwashed with IPE
  9. customdried

Sources & evidence

ORD record
ord-084e2a3a6a5f48fa9536dd58c715d186
Source dataset
uspto-grants-1997_09
Patent number
US05670452

Reaction notes

Loading…