Sodium Hydroxide → 7-Chloro-2,3-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrolo[2,3-d]pyridazine

HRID 433880ノート

反応式

HRID 433880 の反応式
P(Cl)(Cl)([Cl:3])=O.[CH3:6][C:7]1[N:16]([CH2:17][C@H:18]2[CH2:20][C@@H:19]2[CH3:21])[C:10]2[C:11](=O)[NH:12][N:13]=[CH:14][C:9]=2[C:8]=1[CH3:22].[OH-].[Na+]>O>[Cl:3][C:11]1[N:12]=[N:13][CH:14]=[C:9]2[C:8]([CH3:22])=[C:7]([CH3:6])[N:16]([CH2:17][C@H:18]3[CH2:20][C@@H:19]3[CH3:21])[C:10]=12

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 121104562,3-Dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]-6,7-dihydropyrrolo[2,3-d]pyridazin-7-one

生成物 1

HCID 121104577-Chloro-2,3-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrolo[2,3-d]pyridazine収率 92%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

Phosphorus oxychloride (55 ml, 590 mmol) was added to 2,3-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]-6,7-dihydropyrrolo[2,3-d]pyridazin-7-one (6.95 g, 30.1 mmol) and the mixture was stirred at 90° C. for 3.5 hours. After this time the reaction mixture was cooled to room temperature and poured dropwise into iced water. The aqueous solution was neutralized with 5N aqueous sodium hydroxide solution and extracted with methylene chloride. The extract was washed with water, dried over anhydrous magnesium sulfate and then concentrated in vacuo. Hexane was added to the residue and the precipitate was collected by filtration to afford the desired compound (6.90 g, 92.0%) as a pale yellow powder.

後処理

  1. temperatureAfter this time the reaction mixture was cooled to room temperature
  2. extractionextracted with methylene chloride
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. additionHexane was added to the residue
  7. filtrationthe precipitate was collected by filtration

出典と根拠

ORDレコード
ord-47680bc69de6472c974cbe5a1310542d
出典データセット
uspto-grants-2003_12
特許番号
US06670360B2

反応ノート

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