Sodium hydride → 6-chloro-N-(6-(piperidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine

HRID 1755288Notes

Reaction equation

HRID 1755288 reaction equation
[N:1]1([C:7]2[N:12]=[C:11]([NH2:13])[CH:10]=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[C:17]1[C:18]2[N:19]([CH:24]=[CH:25][N:26]=2)[N:20]=[C:21]([Cl:23])[CH:22]=1.[NH4+].[Cl-]>CN(C=O)C>[Cl:23][C:21]1[CH:22]=[C:17]([NH:13][C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[N:12]=2)[C:18]2[N:19]([CH:24]=[CH:25][N:26]=2)[N:20]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 18771896HCID 18771896, compoundHCID 468352698-Bromo-6-chloroimidazo(1,2-b)pyridazine

Product 1

HCID 715343386-chloro-N-(6-(piperidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amineYield 24.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(piperidin-1-yl)pyridin-2-amine (0.725 g, 4.12 mmol) in DMF (8 mL) was added NaH (0.11 g, 60% dispersion in mineral oil, 4.18 mmol) and the mixture stirred for 0.5 h. To this mixture was added 8-bromo-6-chloroimidazo[1,2-b]pyridazine (0.384 g, 1.65 mmol) under N2. The mixture was stirred at room temperature for 16 h. The resulting mixture was treated with a saturated NH4Cl solution (50 mL), extracted with ether (80 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=3:1) to give 6-chloro-N-(6-(piperidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (0.13 g, 24.1%) as a yellow solid. LC-MS: [M+H]+, 329.0, 331.0, tR=1.912 min

Workup

  1. stirringThe mixture was stirred at room temperature for 16 h
  2. extractionextracted with ether (80 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-abb8bcb1f8e748e39f55c3b2c837ed63
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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