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

HRID 870705Notes

Reaction equation

HRID 870705 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 866964073-bromo-N-(2-(tert-butoxy)ethyl)imidazo[1,2-b]pyridazin-6-amineYield 2.6%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

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].

Workup

  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

Sources & evidence

ORD record
ord-58ce1a2c39fd41d7bf81420f3adb7e21
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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