Picolinoyl Chloride Hydrochloride → HCID 57505529, compound

HRID 1667974Notes

Reaction equation

HRID 1667974 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[N:14]=2)[N:11]=1.Cl.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31](Cl)=[O:32].C(=O)([O-])O.[Na+]>CN1CCCC1=O>[CH:18]1([C:16]([NH:15][C:13]2[N:14]=[C:9]3[CH:8]=[CH:7][C:6]([O:5][C:4]4[CH:3]=[C:2]([NH:1][C:31]([C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][N:25]=5)=[O:32])[CH:23]=[CH:22][CH:21]=4)=[N:11][N:10]3[CH:12]=2)=[O:17])[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 135033Picolinoyl Chloride HydrochlorideHCID 516892Sodium BicarbonateHCID 57386059N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57505529HCID 57505529, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (155 mg, 0.50 mmol) in N-methylpyrrolidone (3 mL) was added pyridine-2-carbonylchloride hydrochloride (107 mg, 0.60 mmol), and the mixture was stirred at room temperature for 18 hr. A 5% aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→80/20) and crystallized from ethyl acetate to give the title compound (131 mg, yield 63%) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→80/20)
  4. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-caff116429624b7b81d18a878111b3ce
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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