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

HRID 433880노트

반응식

HRID 433880 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-47680bc69de6472c974cbe5a1310542d
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06670360B2

반응 노트

불러오는 중…