Citric Acid → HCID 22281907, compound

HRID 1368596Notes

Reaction equation

HRID 1368596 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([C:13]2[CH:21]=[CH:20][C:16]3[O:17][CH2:18][O:19][C:15]=3[CH:14]=2)=[C:11]([NH2:22])[N:10]([CH3:23])[N:9]=1)(=O)C.[CH:24]([C:27]1[CH:28]=[CH:29][C:30]([S:33](Cl)(=[O:35])=[O:34])=[N:31][CH:32]=1)([CH3:26])[CH3:25].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[O:17]1[C:16]2[CH:20]=[CH:21][C:13]([C:12]3[C:8]([O:7][CH2:6][CH2:5][OH:4])=[N:9][N:10]([CH3:23])[C:11]=3[NH:22][S:33]([C:30]3[CH:29]=[CH:28][C:27]([CH:24]([CH3:26])[CH3:25])=[CH:32][N:31]=3)(=[O:34])=[O:35])=[CH:14][C:15]=2[O:19][CH2:18]1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 222819185-Isopropylpyridine-2-sulfonyl chlorideHCID 23400310HCID 23400310, compound

Product 1

HCID 22281907HCID 22281907, compoundYield 2.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 2-{[5-amino-4-(1,3-benzodioxol-5-yl)-1-methyl-1H-pyrazol-3-yl]oxy}ethyl acetate (Preparation 33) (500 mg) in anhydrous pyridine (5 ml) at room temperature and under an atmosphere of nitrogen was added 4-dimethylaminopyridine (191 mg) and 5-isopropyl-2-pyridinesulfonyl chloride (1.72 g). After being left to reflux overnight, the reaction mixture was poured onto saturated citric acid solution (50 ml) and extracted with ethyl acetate (2×50 ml). The organic fractions were washed with brine (50 ml), followed by drying over magnesium sulfate, filtering and concentration under reduced pressure. To a solution of the residue in ethanol (50 ml) was added sodium hydroxide solution (5 ml of 2M). The mixture was stirred overnight before being concentrated to approximately 5 ml under reduced pressure and partitioned between ethyl acetate (2×100 ml) and saturated citric acid solution (100 ml). Washing of the organic fractions with brine (100 ml), drying over magnesium sulfate, filtering and concentration under reduced pressure afforded a brown residue. Purification by column chromatography on silica gel (5 g), eluting in an isocratic fashion with ethyl acetate:hexane (2:1) afforded the title compound as a gum (18 mg).

Workup

  1. waitAfter being left
  2. temperatureto reflux overnight
  3. extractionextracted with ethyl acetate (2×50 ml)
  4. washThe organic fractions were washed with brine (50 ml)
  5. dry with materialby drying over magnesium sulfate
  6. filtrationfiltering
  7. concentrationconcentration under reduced pressure
  8. additionTo a solution of the residue in ethanol (50 ml) was added sodium hydroxide solution (5 ml of 2M)
  9. concentrationbefore being concentrated to approximately 5 ml under reduced pressure
  10. custompartitioned between ethyl acetate (2×100 ml) and saturated citric acid solution (100 ml)
  11. washWashing of the organic fractions with brine (100 ml)
  12. dry with materialdrying over magnesium sulfate
  13. filtrationfiltering
  14. concentrationconcentration under reduced pressure
  15. customafforded a brown residue
  16. customPurification by column chromatography on silica gel (5 g)
  17. washeluting in an isocratic fashion with ethyl acetate:hexane (2:1)

Sources & evidence

ORD record
ord-51691f9241744f05859006e4e25a8a6f
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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