Ammonium → HCID 17835906, compound

HRID 1173138Notes

Reaction equation

HRID 1173138 reaction equation
C(OC([C:6]1C2[C:10](=[CH:11][C:12]([NH2:16])=CC=2)[N:9]=[C:8](Cl)[CH:7]=1)=O)C.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([S:24](Cl)(=[O:26])=[O:25])[CH:19]=1.[OH-].[Na+].[ClH:30].C(Cl)(=O)C(Cl)=O.[NH4+:37].FC(F)(F)C(OC(=O)C(F)(F)F)=O.O1[CH2:55][CH2:54][CH2:53][CH2:52]1>[Cl-].[Na+].O.N1C=CC=CC=1.CN(C)C=O.C(O)C>[Cl:30][C:53]1[CH:54]=[C:55]2[C:10](=[C:11]([C:12]#[N:16])[CH:52]=1)[N:9]=[CH:8][C:7]([NH:37][S:24]([C:20]1[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=1)(=[O:26])=[O:25])=[CH:6]2

Participants

13

Reactant 8

HCID 223AmmoniumHCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 3164136Pyridine-3-sulfonyl chlorideHCID 22674043HCID 22674043, compound

Product 1

HCID 17835906HCID 17835906, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent2×

Procedure

764 mg of white crystals were obtained using 3.0 mg (13 mmol, Production Example 13b) of ethyl-7-amino-2-chloroquinoline-4-carboxylate and 2.3 g (13 mmol) of 3-pyridinesulfonyl chloride in the same manner as in Synthetic Example 1b. An aqueous 1 N sodium hydroxide solution (0.5 ml) was added to an ethanol solution (6 ml) of 108 mg (0.28 mmol) of the white crystals, followed by stirring overnight. An aqueous 1 N hydrochloric acid solution was added to the reaction solution, followed by extracting with ethyl acetate twice. The organic layer was washed with brine, dried over magnesium sulfate and concentrated, to give the residue. Under ice-cooling, oxalyl chloride (0.04 ml) and one droplet of dimethylformamide were added to a tetrahydrofuran solution (10 ml) containing the residue, followed by stirring at room temperature for 30 minutes. After 30 minutes, an aqueous saturated ammonium solution (5 ml) was added thereto, followed by stirring for further 10 minutes. Brine was added to the reaction solution, followed by extracting with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated, to give the residue. Under ice-cooling, pyridine (0.06 ml) and trifluoroacetic acid anhydride (0.05 ml) were added to a tetrahydrofuran solution (6 ml) containing the residue, followed by stirring at room temperature for 30 minutes. Brine was added to the reaction solution, followed by extracting with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by silica gel chromatography, to give 37 mg of the title compound.

Workup

  1. extractionby extracting with ethyl acetate twice
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give the residue
  6. temperatureUnder ice-cooling
  7. additioncontaining the residue
  8. stirringby stirring at room temperature for 30 minutes
  9. waitAfter 30 minutes
  10. stirringby stirring for further 10 minutes
  11. extractionby extracting with ethyl acetate
  12. dry with materialThe organic layer was dried over magnesium sulfate
  13. concentrationconcentrated
  14. customto give the residue
  15. temperatureUnder ice-cooling
  16. additioncontaining the residue
  17. stirringby stirring at room temperature for 30 minutes
  18. extractionby extracting with ethyl acetate
  19. dry with materialThe organic layer was dried over magnesium sulfate
  20. concentrationconcentrated
  21. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-37a2ba80f9744e15aa80b20aada00f93
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

Loading…