Water → 2,3-Dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]-6,7-dihydropyrrolo[2,3-d]pyridazin-7-one

HRID 433879노트

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HRID 433879 반응식
O.[NH2:2][NH2:3].[CH:4]([C:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[N:8]([CH2:13][C@H:14]2[CH2:16][C@@H:15]2[CH3:17])[C:7]=1[C:18]([O:20]C)=O)=O.O>C(O)(=O)C>[CH3:12][C:9]1[N:8]([CH2:13][C@H:14]2[CH2:16][C@@H:15]2[CH3:17])[C:7]2[C:18](=[O:20])[NH:2][N:3]=[CH:4][C:6]=2[C:10]=1[CH3:11]

참가 물질

5

반응물 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 12110455Methyl 3-formyl-4,5-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrole-2-carboxylate

생성물 1

HCID 121104562,3-Dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]-6,7-dihydropyrrolo[2,3-d]pyridazin-7-one수율 95.1%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
90 °C

실험 절차

Hydrazine hydrate (1.92 g, 38.4 mmol) was added to a solution of methyl 3-formyl-4,5-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrole-2-carboxylate (7.96 g, 31.9 mmol) in acetic acid (38 ml) and the mixture was stirred at 90° C. for 1 hour. After this time, the reaction mixture was cooled to room temperature, poured into iced water and filtered. The crude crystals were washed with water and dissolved in a mixture of chloroform and methanol (9:1). The organic layer was separated, washed with saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was removed in vacuo and to the residue was added a mixture of toluene and hexane. The precipitate was collected by filtration to afford the desired compound (7.02 g, 95.0%) as a pale yellowish white powder.

후처리

  1. temperatureAfter this time, the reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washThe crude crystals were washed with water
  4. dissolutiondissolved in a mixture of chloroform and methanol (9:1)
  5. customThe organic layer was separated
  6. washwashed with saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed in vacuo and to the residue
  9. additionwas added
  10. additiona mixture of toluene and hexane
  11. filtrationThe precipitate was collected by filtration

출처 및 근거

ORD 기록
ord-d2cfd1178aa44ecbbc9a563a3c5b8e1f
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06670360B2

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