Triethylamine → 3-bromo-N-(2-(tert-butoxy)ethyl)imidazo[1,2-b]pyridazin-6-amine

HRID 870705Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870705
[Br:1][C:2]1[N:6]2[N:7]=[C:8](F)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.C(N(CC)CC)C.[C:19]([O:23][CH2:24][CH2:25][NH2:26])([CH3:22])([CH3:21])[CH3:20]>C(O)(C)C.C(OCC)(=O)C>[Br:1][C:2]1[N:6]2[N:7]=[C:8]([NH:26][CH2:25][CH2:24][O:23][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 219146142-(Tert-butoxy)ethanamineHCID 866963183-Bromo-6-fluoroimidazo[1,2-b]pyridazine

Produkt 1

HCID 866964073-bromo-N-(2-(tert-butoxy)ethyl)imidazo[1,2-b]pyridazin-6-amineAusbeute 2,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 3-bromo-6-fluoroimidazo[1,2-b]pyridazine (216 mg, 1.0 mmol), triethyl amine (0.35 mL, 2.5 mmol) and 2-(tert-butoxy)ethanamine (180 mg, 1.5 mmol) in isopropanol (2 mL) was heated at 65° C. for overnight. The mixture was cooled, diluted with ethyl acetate and washed with water. The organic layer was dried over MgSO4 and concentrated to give brown solid as crude in quantitative yield for further synthesis. 20 mg was further purified by Prep HPLC to give pure 3-bromo-N-(2-(tert-butoxy)ethyl)imidazo[1,2-b]pyridazin-6-amine as white solid (8 mg). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.57 (d, J=9.85 Hz, 1H), 7.42 (s, 1H), 6.76 (d, J=9.60 Hz, 1H), 4.56 (s, 1H), 3.67 (t, J=5.94 Hz, 2H), 3.53 (t, J=5.94 Hz, 2H), 1.24 (s, 9H) LRMS (ESI) m/e 315.0 [(M+H)+, calcd for C12H18BrN4O 314.2].

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. washwashed with water
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customto give brown solid as crude in quantitative yield
  6. customfor further synthesis
  7. custom20 mg was further purified by Prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-58ce1a2c39fd41d7bf81420f3adb7e21
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969565B2

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