Dimethylformamide → 6-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyridazine-3-carboxylic acid isopropylamide

HRID 548877Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 548877
I[C:2]1[N:7]=[N:6][C:5]([NH:8][CH2:9][C:10]2[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])=[CH:4][CH:3]=1.[CH:22]([NH2:25])([CH3:24])[CH3:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN([CH:48]=[O:49])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:22]([NH:25][C:48]([C:2]1[N:7]=[N:6][C:5]([NH:8][CH2:9][C:10]2[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])=[CH:4][CH:3]=1)=[O:49])([CH3:24])[CH3:23]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6363IsopropylamineHCID 11776TriphenylphosphineHCID 86630896(6-Iodo-pyridazine-3-yl)-(5-methyl-3-phenyl-isoxazol-4ylmethyl)-amine

Produkt 1

HCID 671580036-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyridazine-3-carboxylic acid isopropylamideAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 167845palladium(II) acetateKatalysator

Versuchsvorschrift

To a solution of (6-iodo-pyridazine-3-yl)-(5-methyl-3-phenyl-isoxazol-4ylmethyl)-amine (300 mg, 0.76 mmol) in DMF (3 mL) was added isopropylamine (0.66 ml, 7.6 mmol), triphenylphosphine (20 mg, 0.08 mmol) and palladium(II) acetate (17 mg, 0.08 mmol). The resulting mixture was stirred at room temperature for 16 h under a carbon monoxide atmosphere. After evaporation of the solvent the residue was extracted (ethyl acetate/water). The organic phase was dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 20:80) to afford the title compound (55 mg, 20%) as a light yellow oil. MS: m/e=352.3 [M+H]+.

Aufarbeitung

  1. customAfter evaporation of the solvent the residue
  2. extractionwas extracted (ethyl acetate/water)
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 20:80)

Quellen und Nachweise

ORD-Eintrag
ord-3f07ee7f6ddf430eb35ae002a6a06866
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943619B2

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