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

HRID 1582321Notes

Reaction equation

HRID 1582321 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9c370f58ee164b7fb93e0f718e61f0a4
Source dataset
uspto-grants-2004_05
Patent number
US06734181B2

Reaction notes

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