Sodium Hydroxide → 7-Chloro-2,3-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrolo[2,3-d]pyridazine
Reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][C:7]1[N:16]([CH2:17][C@H:18]2[CH2:20][C@@H:19]2[CH3:21])[C:10]2[C:11](=O)[NH:12][N:13]=[CH:14][C:9]=2[C:8]=1[CH3:22].[OH-].[Na+]>O>[Cl:3][C:11]1[N:12]=[N:13][CH:14]=[C:9]2[C:8]([CH3:22])=[C:7]([CH3:6])[N:16]([CH2:17][C@H:18]3[CH2:20][C@@H:19]3[CH3:21])[C:10]=12Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
Phosphorus oxychloride (55 ml, 590 mmol) was added to 2,3-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]-6,7-dihydropyrrolo[2,3-d]pyridazin-7-one (6.95 g, 30.1 mmol) and the mixture was stirred at 90° C. for 3.5 hours. After this time the reaction mixture was cooled to room temperature and poured dropwise into iced water. The aqueous solution was neutralized with 5N aqueous sodium hydroxide solution and extracted with methylene chloride. The extract was washed with water, dried over anhydrous magnesium sulfate and then concentrated in vacuo. Hexane was added to the residue and the precipitate was collected by filtration to afford the desired compound (6.90 g, 92.0%) as a pale yellow powder.
Workup
- temperatureAfter this time the reaction mixture was cooled to room temperature
- extractionextracted with methylene chloride
- washThe extract was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated in vacuo
- additionHexane was added to the residue
- filtrationthe precipitate was collected by filtration
Sources & evidence
- ORD record
- ord-47680bc69de6472c974cbe5a1310542d
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06670360B2
Reaction notes
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