6-Amino-3-chloropyridazine → Ethyl 6-chloro-3-methylimidazo[1,2-b]pyridazine-2-carboxylate

HRID 1067602노트

반응식

HRID 1067602 반응식
[NH2:1][C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.Br[CH:10]([CH3:17])[C:11](=O)[C:12]([O:14][CH3:15])=[O:13].[CH2:18](N(C(C)C)C(C)C)C>C(O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([C:10]([CH3:17])=[C:11]([C:12]([O:14][CH2:15][CH3:18])=[O:13])[N:1]=2)[N:4]=1

참가 물질

5

반응물 3

HCID 216436-Amino-3-chloropyridazineHCID 81531DiisopropylethylamineHCID 11183175Methyl 3-bromo-2-oxobutanoate

생성물 1

HCID 22989254Ethyl 6-chloro-3-methylimidazo[1,2-b]pyridazine-2-carboxylate

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

5.83 g of 3-amino-6-chloropyridazine was suspended in 70 ml of ethanol; 9.75 g of methyl 3-bromo-2-oxobutyrate and 8.6 ml of N-ethyldiisopropylamine were added, followed by thermal refluxing for 5 hours. After cooling, the mixture was concentrated under reduced pressure; the residue was ajusted to pH 7 by the addition of an aqueous solution of sodium hydrogen carbonate and extracted with ethyl acetate-tetrahydrofuran (1:1); the extract was washed with saline and dried with magnesium sulfate. The dry product was concentrated under reduced pressure; ethyl acetate was added to the residue; the crystal precipitated was collected by filtration, washed with ethyl acetate and dried to yield 3.9 g of the title compound.

후처리

  1. customrefluxing for 5 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionthe residue was ajusted to pH 7 by the addition of an aqueous solution of sodium hydrogen carbonate
  5. extractionextracted with ethyl acetate-tetrahydrofuran (1:1)
  6. washthe extract was washed with saline
  7. dry with materialdried with magnesium sulfate
  8. concentrationThe dry product was concentrated under reduced pressure
  9. additionethyl acetate was added to the residue
  10. customthe crystal precipitated
  11. filtrationwas collected by filtration
  12. washwashed with ethyl acetate
  13. customdried

출처 및 근거

ORD 기록
ord-eca603375f224310a231fc6a2169fef8
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248740B1

반응 노트

불러오는 중…