Ammonia → 2,5-difluoro-4-[2-pyridazin-4-yl-4-(trifluoromethyl)phenoxy]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

HRID 46253

Reaktionsgleichung

Reaktionsgleichung von HRID 46253
COC1C=C(OC)C=CC=1C[N:6]([C:19]1[S:23][N:22]=[CH:21][N:20]=1)[S:7]([C:10]1[CH:15]=[C:14]([F:16])[C:13](F)=[CH:12][C:11]=1[F:18])(=[O:9])=[O:8].[N:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[CH:38][C:37]=2[OH:46])=[CH:32][N:31]=1.C(=O)([O-])[O-].[K+].[K+].Cl.FC(F)(F)C(O)=O.N>CN(C)C=O.ClCCl.CO>[F:18][C:11]1[CH:12]=[C:13]([O:46][C:37]2[CH:38]=[CH:39][C:40]([C:42]([F:43])([F:44])[F:45])=[CH:41][C:36]=2[C:33]2[CH:34]=[CH:35][N:30]=[N:31][CH:32]=2)[C:14]([F:16])=[CH:15][C:10]=1[S:7]([NH:6][C:19]1[S:23][N:22]=[CH:21][N:20]=1)(=[O:8])=[O:9]

Komponenten

10

Edukt 6

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 59436583N-(2,4-Dimethoxybenzyl)-2,4,5-trifluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamideHCID 1357416972-(Pyridazin-4-yl)-4-(trifluoromethyl)phenol

Produkt 1

HCID 468413512,5-difluoro-4-[2-pyridazin-4-yl-4-(trifluoromethyl)phenoxy]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittel4×HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

The mixture of N-(2,4-dimethoxybenzyl)-2,4,5-trifluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 647, 44 mg, 0.10 mmol), 2-pyridazin-4-yl-4-(trifluoromethyl)phenol (Preparation 712, 34 mg, 0.10 mmol), and potassium carbonate (55 mg, 0.40 mmol) in N,N-dimethylformamide (1.0 ml) was stirred at room temperature for 24 hours. The reaction mixture was poured into aqueous 2 M hydrochloric acid solution (5.0 ml) and filtered to give a solid. The solid was dissolved in dichloromethane (1.0 ml) and trifluoroacetic acid (1.0 ml) was added to the solution. The resulting solution was stirred for 16 hours. Methanol (5.0 ml) was added to the reaction mixture and filtered off polymeric solid. The filtrate was concentrated in vacuo to give a residue. The residue was passed through a 5 g SCX™ column with 1:1 dichloromethane:methanol solution and then 1:0.75:0.25 dichloromethane:methanol:7N ammonia solution in methanol. The filtrate was concentrated in vacuo and purified by HPLC. Yield 7.3 mg, 14%.

Aufarbeitung

  1. filtrationfiltered
  2. customto give a solid
  3. stirringThe resulting solution was stirred for 16 hours
  4. filtrationfiltered off polymeric solid
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto give a residue
  7. concentrationThe filtrate was concentrated in vacuo
  8. custompurified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-8daee7a4864144e99b62da57688e9470
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541588B2

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