Diisopropylethylamine → (5-Chloro-2-fluorophenyl)(1-(3-chloropyrido[3,4-b]pyrazin-2-yl)piperidin-4-yl)methanone

HRID 713227Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 713227
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([F:17])=[C:7]([C:9]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[O:10])[CH:8]=1.Cl[C:19]1[N:20]=[C:21]2[CH:29]=[CH:28][N:27]=[CH:26][C:22]2=[N:23][C:24]=1[Cl:25].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([F:17])=[C:7]([C:9]([CH:11]2[CH2:12][CH2:13][N:14]([C:19]3[N:20]=[C:21]4[CH:29]=[CH:28][N:27]=[CH:26][C:22]4=[N:23][C:24]=3[Cl:25])[CH2:15][CH2:16]2)=[O:10])[CH:8]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 231227312,3-Dichloropyrido[3,4-b]pyrazineHCID 49761186(5-Chloro-2-fluorophenyl)(piperidin-4-YL)methanone hydrochloride

Produkt 1

HCID 118159129(5-Chloro-2-fluorophenyl)(1-(3-chloropyrido[3,4-b]pyrazin-2-yl)piperidin-4-yl)methanoneAusbeute 101,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of (5-chloro-2-fluorophenyl)(piperidin-4-yl)methanone hydrochloride (153 mg, 0.550 mmol), 2,3-dichloropyrido[3,4-b]pyrazine (100 mg, 0.500 mmol) and DIPEA (261 μL, 1.500 mmol) in DCM (1.67 mL) was stirred at rt for 30 min. The mixture was partitioned between aqueous NH4Cl and EtOAc. The organic layer was filtered through a pad of silica, washing with EtOAc, and the filtrate was concentrated under reduced pressure to give (5-chloro-2-fluorophenyl)(1-(3-chloropyrido[3,4-b]pyrazin-2-yl)piperidin-4-yl)methanone (205.5 mg) as an orange solid. ESI-MS m/z [M+H]+ 405.2.

Aufarbeitung

  1. customThe mixture was partitioned between aqueous NH4Cl and EtOAc
  2. filtrationThe organic layer was filtered through a pad of silica
  3. washwashing with EtOAc
  4. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6a64a1834d694db8ba1b23f654bb6b55
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181249B2

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