Hydrochloric Acid → 5-Chloro-2-fluoro-N-(5-fluoropyridin-2-yl)-4-{[3-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-yl]oxy}benzenesulfonamide

HRID 1619605Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619605
[Cl:1][C:2]1[C:3](F)=[CH:4][C:5]([F:30])=[C:6]([S:8]([N:11](CC2C=CC(OC)=CC=2OC)[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:7]=1.[CH3:32][N:33]1[C:37]([C:38]2[CH:39]=[C:40]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH:41]=[CH:42][C:43]=2[OH:44])=[CH:36][CH:35]=[N:34]1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[Cl:1][C:2]1[C:3]([O:44][C:43]2[CH:42]=[CH:41][C:40]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)=[CH:39][C:38]=2[C:37]2[N:33]([CH3:32])[N:34]=[CH:35][CH:36]=2)=[CH:4][C:5]([F:30])=[C:6]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][N:13]=2)(=[O:9])=[O:10])[CH:7]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 580422485-Chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(5-fluoropyridin-2-yl)benzenesulfonamideHCID 1362008913-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-ol

Produkt 1

HCID 566013805-Chloro-2-fluoro-N-(5-fluoropyridin-2-yl)-4-{[3-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-yl]oxy}benzenesulfonamideAusbeute 63,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

5-Chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(5-fluoropyridin-2-yl)benzenesulfonamide (Preparation 105, 23 mg, 0.04 mmol), 3-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-ol (Preparation 107, 9 mg, 0.04 mmol) and potassium carbonate (15 mg, 0.11 mmol) in dimethyl sulfoxide (1 mL) were stirred at room temperature for 2 hours. The mixture was treated with aqueous 2M HCl (3 mL). The resulting mixture was extracted with dichloromethane (3 mL). The dichloromethane layer was dried through a phase separating cartridge followed by treatment with trifluoroacetic acid (500 μL). The mixture was stirred for 2 hours and allowed to stand at room temperature for 18 hours. The mixture was then treated with a saturated solution of ammonium chloride (5 mL). The dichloromethane layer was separated, dried through a phase separating cartridge and evaporated in vacuo. The residue was purified by preparative HPLC to afford the title compound (14 mg, 45%).

Aufarbeitung

  1. extractionThe resulting mixture was extracted with dichloromethane (3 mL)
  2. dry with materialThe dichloromethane layer was dried through a phase
  3. customseparating cartridge
  4. waitto stand at room temperature for 18 hours
  5. additionThe mixture was then treated with a saturated solution of ammonium chloride (5 mL)
  6. customThe dichloromethane layer was separated
  7. customdried through a phase
  8. customseparating cartridge
  9. customevaporated in vacuo
  10. customThe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-4c1bb89ea4984eb8ac97fea2561b853f
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772293B2

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