Acetonitrile → 3-(5-Cyano-6-(2-(4-fluorophenyl)-2-methylpropylamino)pyridazin-3-yl)benzamide

HRID 869166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 869166
Cl[C:2]1[N:7]=[N:6][C:5]([NH:8][CH2:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)([CH3:12])[CH3:11])=[C:4]([C:20]#[N:21])[CH:3]=1.[NH2:22][C:23]([C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1)=[O:24].C([O-])([O-])=O.[K+].[K+].CC#N>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:20]([C:4]1[CH:3]=[C:2]([C:29]2[CH:30]=[C:25]([CH:26]=[CH:27][CH:28]=2)[C:23]([NH2:22])=[O:24])[N:7]=[N:6][C:5]=1[NH:8][CH2:9][C:10]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)([CH3:12])[CH3:11])#[N:21]

Komponenten

7

Edukt 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 2737814(3-Carbamoylphenyl)boronic acidHCID 866861346-Chloro-3-(2-(4-fluorophenyl)-2-methylpropylamino)pyridazine-4-carbonitrile

Produkt 1

HCID 674530473-(5-Cyano-6-(2-(4-fluorophenyl)-2-methylpropylamino)pyridazin-3-yl)benzamideAusbeute 4,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 6-chloro-3-(2-(4-fluorophenyl)-2-methylpropylamino)pyridazine-4-carbonitrile (550 mg, 1.8 mmol, 1.0 equiv), 3-aminocarbonylphenylboronic acid, pinacol ester (330 mg, 2.0 mmol, 1.1 equiv) and aqueous K2CO3 (2.0 M, 5.0 mL, 5.4 mmol, 3.0 equiv) in dioxane (18 mL) was added Pd(dppf)Cl2 (150 mg, 0.18 mmol, 0.1 equiv). The mixture was stirred at 120° C. for 10 minutes in a microwave and allowed to cool to room temperature. The solvents were evaporated in vacuo, and the residue was dissolved in dichloromethane. The solution was filtered and the solvent dried over Na2SO4. Purification over silica gel using a gradient of 40-80% EtOAc/hexanes gave a yellow solid that was slurried with CH3CN to give the desired product (30 mg, 4.3%) as a yellow solid. m/z=390.2 [M+H]+.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customThe solvents were evaporated in vacuo
  3. dissolutionthe residue was dissolved in dichloromethane
  4. filtrationThe solution was filtered
  5. dry with materialthe solvent dried over Na2SO4
  6. customPurification over silica gel using a gradient of 40-80% EtOAc/hexanes
  7. customgave a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-e96d84480bf9419891bc92e57ba3f416
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969346B2

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