Diisopropylethylamine → 3-((4-(3-(4-chloro-2-fluorophenoxy) azetidin-1-yl)-6-methyl-1,3,5-triazin-2-yl)amino)-N-methylbenzamide

HRID 522920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 522920
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:11][CH:10]([O:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[F:20])[CH2:9]2)[N:5]=[C:4]([CH3:21])[N:3]=1.CCN(C(C)C)C(C)C.[NH2:31][C:32]1[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=1)[C:35]([NH:37][CH3:38])=[O:36]>C(O)(C)C>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH:10]2[CH2:11][N:8]([C:6]3[N:5]=[C:4]([CH3:21])[N:3]=[C:2]([NH:31][C:32]4[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=4)[C:35]([NH:37][CH3:38])=[O:36])[N:7]=3)[CH2:9]2)=[C:14]([F:20])[CH:15]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 6765263-Amino-N-methylbenzamideHCID 866852572-Chloro-4-(3-(4-chloro-2-fluorophenoxy)azetidin-1-yl)-6-methyl-1,3,5-triazine

Produkt 1

HCID 533726083-((4-(3-(4-chloro-2-fluorophenoxy) azetidin-1-yl)-6-methyl-1,3,5-triazin-2-yl)amino)-N-methylbenzamideAusbeute 6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 2-chloro-4-(3-(4-chloro-2-fluorophenoxy)azetidin-1-yl)-6-methyl-1,3,5-triazine (1.0 g, 3.04 mmol) in Isopropanol (10 mL) was added DIPEA (0.8 mL) and 3-amino-N-methylbenzamide (0.460 g, 3.04 mmol) and the reaction mixture was stirred at 80° C. for 24 h. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc (2×40 mL) and water (2×40 mL). The organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided 3-((4-(3-(4-chloro-2-fluorophenoxy) azetidin-1-yl)-6-methyl-1,3,5-triazin-2-yl)amino)-N-methylbenzamide (0.057 g, 6%) as a solid. Observed mass (M+1): 443.1.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with EtOAc (2×40 mL) and water (2×40 mL)
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-eb9ffce00a6c41ed9d9fcd7ec93dfafe
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334269B2

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