Sodium Iodide → HCID 66679973, Verbindung

HRID 1626758

Reaktionsgleichung

Reaktionsgleichung von HRID 1626758
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][C:12](=[O:15])[CH2:13]Cl)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([NH2:30])[CH:24]=2)=[CH:19][CH:18]=1.[I-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][C:12](=[O:15])[CH2:13][NH:30][C:25]2[CH:24]=[C:23]([C:20]3[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=3)[CH:28]=[CH:27][C:26]=2[CH3:29])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Komponenten

6

Edukt 3

HCID 5238Sodium IodideHCID 41798255-Chloro-2-((2-chloroacetyl)amino)benzoic acidHCID 463144304'-Fluoro-4-methylbiphenyl-3-amine

Produkt 1

HCID 66679973HCID 66679973, VerbindungAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

1.0 g (4.0 mmol) of 5-chloro-2-[(chloroacetyl)amino]benzoic acid, 1.78 g (8.9 mmol) of 4′-fluoro-4-methylbiphenyl-3-amine, and 60 mg (0.4 mmol) of sodium iodide were stirred in 3 mL of DMF at 90° C. for 5.5 hours. Thereafter, the reaction mixture was diluted with ethyl acetate and washed with 1N hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography. The separated fractions containing a target compound were combined and condensed. Ethyl acetate was added to the residue, and solids were collected by filtration. The resulting solids were recrystallized using ethyl acetate/n-hexane, thereby giving 334 mg of the target 5-chloro-2-{[N-(4′-fluoro-4-methylbiphenyl-3-yl)glycyl]amino}benzoic acid (yield: 20%).

Aufarbeitung

  1. washwashed with 1N hydrochloric acid
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe obtained crude product
  5. customwas separated
  6. custompurified by silica gel column chromatography
  7. additionThe separated fractions containing a target compound
  8. customcondensed
  9. filtrationwere collected by filtration
  10. customThe resulting solids were recrystallized

Quellen und Nachweise

ORD-Eintrag
ord-f18adea036704c36981cc7781230fb36
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785473B2

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