Pyridine → HCID 86696428, compound

HRID 870723Notes

Reaction equation

HRID 870723 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([NH2:11])=[CH:9][N:10]=2)[N:7]=1.[Br:12][CH2:13][CH2:14][CH2:15][C:16](Cl)=[O:17].N1C=CC=CC=1>C1COCC1.CCOC(C)=O>[Br:12][CH2:13][CH2:14][CH2:15][C:16]([NH:11][C:8]1[N:6]2[N:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]2=[N:10][CH:9]=1)=[O:17]

Participants

6

Reactant 3

HCID 1049PyridineHCID 702254-Bromobutyryl chlorideHCID 107022736-Chloroimidazo[1,2-b]pyridazin-3-amine

Product 1

HCID 86696428HCID 86696428, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1.0 g (5.930 mmol) of 6-chloroimidazo[1,2-b]pyridazin-3-amine dissolved in 15 mL of THF was added 4-bromobutanoyl chloride (1.21 g, 6.52 mmol) and pyridine (0.96 mL, 11.86 mmol). This mixture was stirred for 1 hr at rt, and then diluted with 30 mL EtOAc and quenched with aq. NaHCO3. The organic layer was separated and washed with brine, dried over MgSO4, and concentrated. The solid obtained (1.39 g, 74% yield) was pure enough to be used for the next step without further purification.

Workup

  1. customquenched with aq. NaHCO3
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe solid obtained (1.39 g, 74% yield)
  7. customto be used for the next step without further purification

Sources & evidence

ORD record
ord-07cadc98406d4817a2c9c53c3161d30a
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

Loading…