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

HRID 433879Notes

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.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

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) 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.

Workup

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

Sources & evidence

ORD record: ord-d2cfd1178aa44ecbbc9a563a3c5b8e1f
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06670360B2

Reaction notes

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