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Pyridine → 2-chloro-N-(3-cyano-1-phenyl-1H-pyrazol-5-yl)-4-fluoro-5-(3-fluoropyridin-2-yl)benzamide

HRID 522104
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 522104
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:19][C:20]1[N:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:23]=[C:22]([C:31]#[N:32])[CH:21]=1.N1C=CC=CC=1.CCCP(=O)=O>CCOC(C)=O>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:7][C:3]=1[C:4]([NH:19][C:20]1[N:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:23]=[C:22]([C:31]#[N:32])[CH:21]=1)=[O:6]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 16167369Propylphosphoric anhydride2×HCID 177636545-amino-1-phenyl-1H-pyrazole-3-carbonitrileHCID 1184971782-Chloro-4-fluoro-5-(3-fluoropyridin-2-yl)benzoic acid

Produkt 1

HCID 1184970492-chloro-N-(3-cyano-1-phenyl-1H-pyrazol-5-yl)-4-fluoro-5-(3-fluoropyridin-2-yl)benzamideAusbeute 34,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 2-chloro-4-fluoro-5-(3-fluoropyridin-2-yl)benzoic acid (Preparation 21, 160 mg, 0.59 mmol) in 2-Methyl-THF (3 mL) was added 5-amino-1-phenyl-1H-pyrazole-3-carbonitrile (Preparation 53, 120 mg, 0.65 mmol) and pyridine (0.14 mL, 1.77 mmol). The reaction was heated to 90° C. before the addition of propylphosphonic anhydride (752 mg, 1.18 mmol) and the reaction was continued heating at 90° C. for 16 hours. Further propylphosphonic anhydride (752 mg, 1.18 mmol) was added and the reaction continued to heat at 90° C. for 3 hours. The reaction was cooled to room temperature, diluted with EtOAc (20 mL) and washed with 2M NaOH(aq) (2×20 mL), saturated aqueous NH4Cl solution (20 mL), water (20 mL) and brine (20 mL). The organic layer was dried over magnesium sulphate and concentrated in vacuo. The residue was purified using reverse phase column chromatography eluting from 5-60% MeCN (with 0.1% HCO2H) in water (with 0.1% HCO2H) to afford the title compound (89 mg, 34%).

Aufarbeitung

  1. temperatureto heat at 90° C. for 3 hours
  2. temperatureThe reaction was cooled to room temperature
  3. washwashed with 2M NaOH(aq) (2×20 mL), saturated aqueous NH4Cl solution (20 mL), water (20 mL) and brine (20 mL)
  4. dry with materialThe organic layer was dried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified
  7. washeluting from 5-60% MeCN (with 0.1% HCO2H) in water (with 0.1% HCO2H)

Quellen und Nachweise

ORD-Eintrag
ord-44e54a2c25f2483eb4ff565a07a8f27e
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09328096B2

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