HCID 117640744, Verbindung → N-(5-chloro-6-(6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)-1-(2,2-difluorobenzo [d][1,3]dioxol-5-yl)cyclopropanecarboxamide

HRID 869910Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 869910
[Cl:1][C:2]1[C:3]([C:25]2[CH:26]=[N:27][C:28]([O:31]C)=[CH:29][CH:30]=2)=[N:4][C:5]([NH:8][C:9]([C:11]2([C:14]3[CH:24]=[CH:23][C:17]4[O:18][C:19]([F:22])([F:21])[O:20][C:16]=4[CH:15]=3)[CH2:13][CH2:12]2)=[O:10])=[CH:6][CH:7]=1>O1CCOCC1.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2([C:14]3[CH:24]=[CH:23][C:17]4[O:18][C:19]([F:22])([F:21])[O:20][C:16]=4[CH:15]=3)[CH2:12][CH2:13]2)=[O:10])=[N:4][C:3]=1[C:25]1[CH:30]=[CH:29][C:28](=[O:31])[NH:27][CH:26]=1

Komponenten

4

Edukt 1

HCID 117640744HCID 117640744, Verbindung

Produkt 1

HCID 117640729N-(5-chloro-6-(6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)-1-(2,2-difluorobenzo [d][1,3]dioxol-5-yl)cyclopropanecarboxamideAusbeute 22,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

N-(3-Chloro-6′-methoxy-2,3′-bipyridin-6-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (124 mg, 0.270 mmol) was dissolved in a mixture of 1.2 mL of 1,4-dioxane and 0.6 mL of 4M aqueous hydrochloric acid. This solution was heated at 90° C. for 5 hours. The crude reaction mixture was quenched with triethylamine and then evaporated to dryness. The crude product was then partitioned between dichloromethane and water. The organic layer was separated, dried over sodium sulfate, and then purified on 4 g of silica gel utilizing a gradient of 0-5% methanol in dichloromethane to yield N-(5-chloro-6-(6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide as a white solid (27 mg, 22%). ESI-MS m/z calc. 445.1. found 445.9 (M+1)+. Retention time 1.62 minutes.

Aufarbeitung

  1. customThe crude reaction mixture
  2. customwas quenched with triethylamine
  3. customevaporated to dryness
  4. customThe crude product was then partitioned between dichloromethane and water
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. custompurified on 4 g of silica gel utilizing a gradient of 0-5% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-28bd94c26d434269a656e989206b5da2
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969386B2

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