Water → HCID 58042343, Verbindung

HRID 1619719Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619719
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[CH:9]=2)=[CH:4][C:3]=1[C:16]1[CH:21]=[CH:20][N:19]=[N:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:28][C:29]1[C:30](F)=[CH:31][C:32]([F:55])=[C:33]([S:35]([N:38]([CH2:44][C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][C:46]=2[O:53][CH3:54])[C:39]2[S:40][CH:41]=[N:42][N:43]=2)(=[O:37])=[O:36])[CH:34]=1.O>CS(C)=O.C(OCC)(=O)C>[Cl:28][C:29]1[C:30]([O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[CH:9]=3)=[CH:4][C:3]=2[C:16]2[CH:21]=[CH:20][N:19]=[N:18][CH:17]=2)=[CH:31][C:32]([F:55])=[C:33]([S:35]([N:38]([CH2:44][C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][C:46]=2[O:53][CH3:54])[C:39]2[S:40][CH:41]=[N:42][N:43]=2)(=[O:36])=[O:37])[CH:34]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 580422535-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamideHCID 1362008814'-Hydroxy-3'-pyridazin-4-ylbiphenyl-3-carbonitrile

Produkt 1

HCID 58042343HCID 58042343, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4′-Hydroxy-3′-(pyridazin-4-yl)biphenyl-3-carbonitrile (Preparation 119, 330 mg, 1.21 mmol) and potassium carbonate (334 mg, 2.42 mmol) were dissolved in dimethylsulfoxide (7 mL). Then 5-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide (Preparation 16, 558 mg, 1.21 mmol) was added and the reaction was stirred at room temperature for 2 hours. Water (15 mL) and ethyl acetate (25 mL) were added and the two layers were separated. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with 10% dichloromethane in ethyl acetate to give the title compound (561 mg, 65%).

Aufarbeitung

  1. customthe two layers were separated
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel eluting with 10% dichloromethane in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c36d3cc1b8e34f5aa9055d3ce166f53d
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772293B2

Notizen zur Reaktion

Wird geladen…