Triethylamine → HCID 89228784, Verbindung

HRID 869900Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 869900
[F:1][C:2]1([F:17])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14](Cl)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1.[Cl:18][C:19]1[N:24]=[C:23]([NH2:25])[CH:22]=[C:21]([CH3:26])[C:20]=1[CH3:27].CCN(CC)CC>ClCCl>[Cl:18][C:19]1[N:24]=[C:23]([NH:25][C:14]([C:11]2([C:9]3[CH:8]=[CH:7][C:5]4[O:6][C:2]([F:17])([F:1])[O:3][C:4]=4[CH:10]=3)[CH2:13][CH2:12]2)=[O:15])[CH:22]=[C:21]([CH3:26])[C:20]=1[CH3:27]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 575168501-(2,2-Difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl chlorideHCID 735538296-Chloro-4,5-dimethylpyridin-2-amine

Produkt 1

HCID 89228784HCID 89228784, VerbindungAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride (676 mg, 2.6 mmol) and 6-chloro-4,5-dimethylpyridin-2-amine (314 mg, 2.0 mmol), dichloromethane (7.0 mL) and Et3N (835 μL, 6 mmol) were added. The reaction was stirred at room temperature for 1 hour. The reaction was diluted with dichloromethane and washed with 1N HCl (3×) and saturated aqueous NaHCO3 (3×). The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel to yield N-(6-chloro-4,5-dimethylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (560 mg, 73%). ESI-MS m/z calc. 380.07. found 381.3 (M+1)+. Retention time 2.18 minutes.

Aufarbeitung

  1. washwashed with 1N HCl (3×) and saturated aqueous NaHCO3 (3×)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. customevaporated under reduced pressure
  4. customThe crude product was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f60411c0df664517ac7fed7c5bfc7d11
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969386B2

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