Potassium Carbonate → Tert-butyl 4-{4-[4-(2-chloro-4-{[(2,4-dimethoxybenzyl)(pyrimidin-4-yl)amino]sulfonyl}-5-fluorophenoxy)-4'-(trifluoromethyl)biphenyl-3-yl]pyridin-2-yl}piperazine-1-carboxylate

HRID 1619710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619710
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:18]1[CH:23]=[CH:22][N:21]=[C:20]([N:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]2)[CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:43][C:44]1[C:45](F)=[CH:46][C:47]([F:71])=[C:48]([S:50]([N:53]([CH2:60][C:61]2[CH:66]=[CH:65][C:64]([O:67][CH3:68])=[CH:63][C:62]=2[O:69][CH3:70])[C:54]2[CH:59]=[CH:58][N:57]=[CH:56][N:55]=2)(=[O:52])=[O:51])[CH:49]=1>CS(C)=O>[Cl:43][C:44]1[CH:49]=[C:48]([S:50]([N:53]([CH2:60][C:61]2[CH:66]=[CH:65][C:64]([O:67][CH3:68])=[CH:63][C:62]=2[O:69][CH3:70])[C:54]2[CH:59]=[CH:58][N:57]=[CH:56][N:55]=2)(=[O:51])=[O:52])[C:47]([F:71])=[CH:46][C:45]=1[O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([F:16])([F:17])[F:15])=[CH:12][CH:13]=2)=[CH:4][C:3]=1[C:18]1[CH:23]=[CH:22][N:21]=[C:20]([N:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]2)[CH:19]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 580422515-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(pyrimidin-4-yl)benzenesulfonamideHCID 136200880Tert-butyl 4-(4-(4-hydroxy-4'-(trifluoromethyl)biphenyl-3-yl)pyridin-2-yl)piperazine-1-carboxylate

Produkt 1

HCID 58042259Tert-butyl 4-{4-[4-(2-chloro-4-{[(2,4-dimethoxybenzyl)(pyrimidin-4-yl)amino]sulfonyl}-5-fluorophenoxy)-4'-(trifluoromethyl)biphenyl-3-yl]pyridin-2-yl}piperazine-1-carboxylateAusbeute 85,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 4-(4-(4-hydroxy-4′-(trifluoromethyl)biphenyl-3-yl)pyridin-2-yl)piperazine-1-carboxylate (Preparation 114, 200 mg, 0.401 mmol) in dimethyl sulfoxide (5 mL) was added potassium carbonate (111 mg, 0.802 mmol) followed by 5-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(pyrimidin-4-yl)benzenesulfonamide (Preparation 110, 182 mg, 0.401 mmol). The reaction mixture was stirred at room temperature for 2 hours and then partitioned between ethyl acetate (20 mL) and water (10 mL). The organic layer was separated, dried over anhydrous MgSO4, filtered and evaporated. The residue was purified by flash chromatography on silica gel eluting with 30% heptane in ethyl acetate to give the title compound (320 mg, 85%) as yellow foam.

Aufarbeitung

  1. custompartitioned between ethyl acetate (20 mL) and water (10 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel eluting with 30% heptane in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f8ded585da0e435fba677a291e329711
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772293B2

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