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

HRID 1582321ノート

反応式

HRID 1582321 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>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

4

反応物 2

HCID 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) at room temperature and the mixture was stirred at 90° C. for 1 hour. After the reaction was completed, the reaction mixture was cooled to room temperature and poured into ice-water. The crude crystals were collected by filtration, washed with water and dissolved in a mixture of chloroform and methanol (9:1). The organic layer was separated, washed with a 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. temperaturethe reaction mixture was cooled to room temperature
  2. filtrationThe crude crystals were collected by filtration
  3. washwashed with water
  4. dissolutiondissolved in a mixture of chloroform and methanol (9:1)
  5. customThe organic layer was separated
  6. washwashed with a 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-9c370f58ee164b7fb93e0f718e61f0a4
出典データセット
uspto-grants-2004_05
特許番号
US06734181B2

反応ノート

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