Triethylamine → (S)-(4-(1-chloropyrido[3,4-d]pyridazin-4-yl)-2-methylpiperazin-1-yl)(piperidin-1-yl)methanone
Reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][C@@H:10]([CH3:14])[CH2:9]2)=[C:4]2[CH:15]=[N:16][CH:17]=[CH:18][C:3]=12.C(N(CC)CC)C.[N:26]1([C:32](Cl)=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:32]([N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[O:33])[C@@H:10]([CH3:14])[CH2:9]2)=[C:4]2[CH:15]=[N:16][CH:17]=[CH:18][C:3]=12Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (S)-1-chloro-4-(3-methylpiperazin-1-yl)pyrido[3,4-d]pyridazine 4 (500 mg, 1.90 mmol) in 10 mL of CH2Cl2 was added triethylamine (529 μl, 3.79 mmol), followed by 1-piperidinecarbonyl chloride (364 μl, 2.47 mmol). The reaction was allowed to stir overnight and then diluted with 100 mL of ethyl acetate. The crude mixture was washed with 1×10 mL of sat. NaHCO3, 1×10 mL of water, and 1×10 mL of brine. The organic layer was dried over MgSO4, filtered, and concentrated. Purification by column chromatography afforded (S)-(4-(1-chloropyrido[3,4-d]pyridazin-4-yl)-2-methylpiperazin-1-yl)(piperidin-1-yl)methanone 7.
Workup
- washThe crude mixture was washed with 1×10 mL of sat. NaHCO3, 1×10 mL of water, and 1×10 mL of brine
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customPurification by column chromatography
Sources & evidence
- ORD record
- ord-5113eff57085441097ae04a1cd3ebf3e
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08222251B2
Reaction notes
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