4-Fluoroaniline → 4-(3-Fluoro-4-{[1-(4-fluorophenylcarbamoyl)cyclopropanecarbonyl]amino}phenoxy)pyridine-2-carboxamide

HRID 2066255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2066255
[C:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]3([C:23]([OH:25])=O)[CH2:22][CH2:21]3)=[O:19])=[C:13]([F:26])[CH:12]=2)[CH:7]=[CH:6][N:5]=1)(=[O:3])[NH2:2].[F:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>O1CCCC1>[F:26][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=1[NH:17][C:18]([C:20]1([C:23](=[O:25])[NH:32][C:31]2[CH:33]=[CH:34][C:28]([F:27])=[CH:29][CH:30]=2)[CH2:22][CH2:21]1)=[O:19])[O:10][C:8]1[CH:7]=[CH:6][N:5]=[C:4]([C:1]([NH2:2])=[O:3])[CH:9]=1

Komponenten

5

Edukt 3

HCID 97314-FluoroanilineHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 686917891-[4-(2-Carbamoylpyridin-4-yl)oxy-2-fluorophenylaminocarbonyl]cyclopropanecarboxylic acid

Produkt 1

HCID 595970164-(3-Fluoro-4-{[1-(4-fluorophenylcarbamoyl)cyclopropanecarbonyl]amino}phenoxy)pyridine-2-carboxamideAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 1-[4-(2-carbamoylpyridin-4-yl)oxy-2-fluorophenylaminocarbonyl]cyclopropanecarboxylic acid (743 mg) and 4-fluoroaniline (459 mg) in tetrahydrofuran (30 ml) was added 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (1.22 g), followed by stirring at room temperature for 7.5 hr. The reaction mixture was partitioned between ethyl acetate and an aqueous solution of sodium hydrogencarbonate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and the resultant residue was suspended by addition of tert-butyl methyl ether—ethyl acetate (1:1, 20 ml). The solid was collected by filtration and dried under aeration to provide the titled compound as a white solid (815 mg, 87%).

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. additionthe resultant residue was suspended by addition of tert-butyl methyl ether—ethyl acetate (1:1, 20 ml)
  6. filtrationThe solid was collected by filtration
  7. customdried under aeration

Quellen und Nachweise

ORD-Eintrag
ord-3bb6459f1797415ea579d60c36363426
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288538B2

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