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

HRID 706848Notes

Reaction equation

HRID 706848 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 867095663-(2-(Imidazo[1,2-b]pyridazin-3-yl)ethynyl)piperidineYield 121.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 (1 H, d, J=4.5 Hz), 7.93-7.97 (1 H, dd, J=1.8 and 9.0 Hz), 7.91 (1 H, s), 7.05-7.09 (1 H, dd, J=4.5 and 9.0 Hz), 2.82-2.98 (4 H, m), 2.08-2.11 (1 H, m), 1.75-1.84 (2 H, m), 1.53-1.58 (2 H, m).

Workup

  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

Sources & evidence

ORD record
ord-226936f991934786888d4488629699f9
Source dataset
uspto-grants-2015_11
Patent number
US09174996B2

Reaction notes

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