Trifluoroacetic acid → 3-(2-(Imidazo[1,2-b]pyridazin-3-yl)ethynyl)piperidine

HRID 535863Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 535863
C([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]#[C:15][C:16]2[N:20]3[N:21]=[CH:22][CH:23]=[CH:24][C:19]3=[N:18][CH:17]=2)[CH2:9]1)(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:18]1[CH:17]=[C:16]([C:15]#[C:14][CH:10]2[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)[N:20]2[C:19]=1[CH:24]=[CH:23][CH:22]=[N:21]2

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 867095651-BOC-3-(2-(imidazo[1,2-b]pyridazin-3-yl)ethynyl)piperidine

Produkt 1

HCID 867095663-(2-(Imidazo[1,2-b]pyridazin-3-yl)ethynyl)piperidineAusbeute 121,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-BOC-3-(2-(imidazo[1,2-b]pyridazin-3-yl)ethynyl)piperidine (0.39 g, 1.2 mmol) in CH2Cl2 (10 mL) was added TFA (1.23 g, 10.8 mmol), the mixture was stirred at rt overnight and evaporated in vacuo. To the residue was added 10 mL 10% K2CO3 solution, extracted with EtOAc (20 mL×3), dried with Na2SO4, after filtration, and the filtrate was evaporated under reduced pressure to give 0.33 g product as yellow oil (107.0%). 1H NMR (300 MHz, CDCl3) δ: 8.43 (1H, d, J=4.5 Hz), 7.93-7.97 (1H, dd, J=1.8 and 9.0 Hz), 7.91 (1H, s), 7.05-7.09 (1H, dd, J=4.5 and 9.0 Hz), 2.82-2.98 (4H, m), 2.08-2.11 (1H, m), 1.75-1.84 (2H, m), 1.53-1.58 (2H, m).

Aufarbeitung

  1. customevaporated in vacuo
  2. additionTo the residue was added 10 mL 10% K2CO3 solution
  3. extractionextracted with EtOAc (20 mL×3)
  4. dry with materialdried with Na2SO4
  5. filtrationafter filtration
  6. customthe filtrate was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7c7dd2d73bca440a8c82e7086fd13038
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859553B2

Notizen zur Reaktion

Wird geladen…