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

HRID 1169141ノート

反応式

HRID 1169141 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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 adjusted 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, dried over magnesium sulfate and 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.

後処理

  1. customrefluxing for 5 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionThe residue was adjusted 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 over magnesium sulfate
  8. concentrationconcentrated 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

出典と根拠

ORDレコード
ord-46f9683357e54fe18f932be32947bf47
出典データセット
uspto-grants-2003_09
特許番号
US06627630B1

反応ノート

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