Tetrahydrofuran → HCID 22989337, compound

HRID 1067600Notes

Reaction equation

HRID 1067600 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][NH:6][C:7]([C:9]1[N:10]=[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[N:13][N:12]2[CH:18]=1)=[O:8])[CH3:2].[Cl:20]N1C(=O)CCC1=O.O1CCCC1>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][NH:6][C:7]([C:9]1[N:10]=[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[N:13][N:12]2[C:18]=1[Cl:20])=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 31398ChlorosuccinimideHCID 22989255N-(6-chloroimidazo-[1,2-b]pyridazine-2-carbonyl)glycine ethyl ester

Product 1

HCID 22989337HCID 22989337, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.86 g of N-(6-chloroimidazo[1,2-b]pyridazine-2-carbonyl)glycine ethyl ester was suspended in 30 ml of ethyl acetate; 1.2 g of N-chlorosuccinimide was added, followed by thermal refluxing for 20 hours. After cooling, 30 ml of tetrahydrofuran was added; the mixture was washed with an aqueous solution of sodium thiosulfate and saline and dried with magnesium sulfate. The dry product was concentrated under reduced pressure; ethyl ether was added to the residue; the crystal precipitated was collected by filtration, washed with ethyl ether and dried to yield 0.552 g of the title compound.

Workup

  1. customrefluxing for 20 hours
  2. temperatureAfter cooling
  3. washthe mixture was washed with an aqueous solution of sodium thiosulfate and saline
  4. dry with materialdried with magnesium sulfate
  5. concentrationThe dry product was concentrated under reduced pressure
  6. additionethyl ether was added to the residue
  7. customthe crystal precipitated
  8. filtrationwas collected by filtration
  9. washwashed with ethyl ether
  10. customdried

Sources & evidence

ORD record
ord-0b2c16e7c07945ffaeb6dfd35490679a
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

Loading…