Dabco → HCID 58042318, compound

HRID 1619628Notes

Reaction equation

HRID 1619628 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[N:2]=1.[Cl:8][C:9]1[CH:10]=[C:11]([S:16](Cl)(=[O:18])=[O:17])[CH:12]=[CH:13][C:14]=1[F:15].N12CCN(CC1)CC2>C(#N)C>[Cl:8][C:9]1[CH:10]=[C:11]([S:16]([NH:7][C:3]2[N:2]=[N:1][CH:6]=[CH:5][CH:4]=2)(=[O:17])=[O:18])[CH:12]=[CH:13][C:14]=1[F:15]

Participants

5

Reactant 3

HCID 9237DabcoHCID 1452223-Chloro-4-fluorobenzenesulphonyl chlorideHCID 230373Aminopyridazine

Product 1

HCID 58042318HCID 58042318, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of pyridazin-3-amine (5.0 g, 52.63 mmol) in anhydrous acetonitrile (250 mL) was added 3-chloro-4-fluorobenzenesulfonyl chloride (12.05 g, 52.63 mmol) followed by 1,4-diazabicyclo[2,2,2]octane (5.9 g, 52.63 mmol). The reaction was stirred at room temperature for 18 hours. A solid was observed which was collected by filtration and washed with acetonitrile. The filtrate was concentrated in vacuo and the resulting residue purified by silica gel column chromatography (0%-10% methanol in chloroform gradient elution) to afford the title compound (5.3 g, 35%)

Workup

  1. filtrationwas collected by filtration
  2. washwashed with acetonitrile
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe resulting residue purified by silica gel column chromatography (0%-10% methanol in chloroform gradient elution)

Sources & evidence

ORD record
ord-d20319f2f97441c3a957062581889763
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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