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

HRID 433879ノート

反応式

HRID 433879 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d2cfd1178aa44ecbbc9a563a3c5b8e1f
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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