Sodium Iodide → 4-imidazo[1,2-b]pyridazin-7-yl-1-(3-piperidin-1-yl-propyl)-1H-pyridin-2-one

HRID 1097314Notes

Reaction equation

HRID 1097314 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[C:7]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([OH:16])[CH:11]=1)[CH:6]=[N:5]2.Cl.Cl[CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[I-].[Na+].C([O-])(O)=O.[Na+]>CN(C=O)C>[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[C:7]([C:10]1[CH:15]=[CH:14][N:13]([CH2:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[C:12](=[O:16])[CH:11]=1)[CH:6]=[N:5]2

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 79624N-(3-chloropropyl)piperidine hydrochlorideHCID 516892Sodium BicarbonateHCID 178515730HCID 178515730, compound

Product 1

HCID 594435094-imidazo[1,2-b]pyridazin-7-yl-1-(3-piperidin-1-yl-propyl)-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

4-Imidazo[1,2-b]pyridazin-7-yl-pyridin-2-ol (1 eq, 0.17 mmol, 36 mg), 1-(3-chloropropyl)piperidine monohydrochloride (1.5 eq, 0.255 mmol, 52 mg) and sodium iodide (1.5 eq, 0.254 mmol, 37.9 mg) are dissolved in DMF (1 ml) and heated at 60° C. for 16 h to give a black solution. The reaction mixture is then poured into aq. sat. NaHCO3 and the organic phase is extracted with CH2Cl2. The organic phase is washed with brine, dried over MgSO4, filtered and evaporated to dryness to afford 4-imidazo[1,2-b]pyridazin-7-yl-1-(3-piperidin-1-yl-propyl)-1H-pyridin-2-one; [M+H]+=338

Workup

  1. customto give a black solution
  2. extractionthe organic phase is extracted with CH2Cl2
  3. washThe organic phase is washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-a2b49cd9be2a42cbbede1bc38ca88ac7
Source dataset
uspto-grants-2012_03
Patent number
US08143253B2

Reaction notes

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