Hydrochloric Acid → 1-(4-(6-(4-Isopropylpiperazin-1-yl)pyridazin-3-yl)phenyl)ethanone
Reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[N:14][C:13]([C:16]3[CH:23]=[CH:22][C:19](C#N)=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[CH3:24][Mg]Br.Cl.[C:28]([O-:31])(O)=O.[Na+]>C1COCC1.C1(C)C=CC=CC=1.C1COCC1>[CH:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[N:15]=[N:14][C:13]([C:16]3[CH:23]=[CH:22][C:19]([C:28](=[O:31])[CH3:24])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)([CH3:3])[CH3:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a suspension of 4-[6-(4-isopropylpiperazin-1-yl)pyridazin-3-yl]benzonitrile (0.36 g, 1.17 mmol, prepared by a similar procedure to that described in Example 1) in dry THF (5 mL) was added a 1.4 M methylmagnesium bromide solution in toluene/THF. The reaction mixture was stirred at room temperature for 24 h, 1 M hydrochloric acid (7 mL) was added and the solution stirred for 1 h. The mixture was made alkaline by addition of excess NaHCO3 solution and extracted with dichloromethane. The organic phase was dried over magnesium sulphate, the solvent was removed and the solid was re-crystallized from ethanol to give the title compound, 163 mg (43%).
Workup
- customprepared by a similar procedure to
- stirringthe solution stirred for 1 h
- extractionextracted with dichloromethane
- dry with materialThe organic phase was dried over magnesium sulphate
- customthe solvent was removed
- customthe solid was re-crystallized from ethanol
Sources & evidence
- ORD record
- ord-e3c523b8da674e179788311628e3eb53
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501739B2
Reaction notes
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