2-Dimethylaminopyridine → N-Propanesulphonyl-6-[N-(5-bromo-2-(2-methylprop-2-en-1-yloxy)benzyl)-N-ethylamino]pyridazine-3-carboxamide
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH2:22][C:23]([CH3:25])=[CH2:24])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]([OH:19])=O)=[CH:13][CH:12]=1)[CH2:9][CH3:10].Cl.CN(C)CCCN=C=NCC.CN(C1C=CC=CN=1)C.[CH2:47]([S:50]([NH2:53])(=[O:52])=[O:51])[CH2:48][CH3:49]>ClCCl.CN(C1C=CN=CC=1)C.CCO.C(Cl)Cl.O.CC#N>[CH2:47]([S:50]([NH:53][C:17]([C:14]1[N:15]=[N:16][C:11]([N:8]([CH2:7][C:6]2[CH:20]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[O:21][CH2:22][C:23]([CH3:25])=[CH2:24])[CH2:9][CH3:10])=[CH:12][CH:13]=1)=[O:19])(=[O:52])=[O:51])[CH2:48][CH3:49]Participants
9
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Procedure
6-[N-(5-Bromo-2-(2-methylprop-2-enyloxy)benzyl)-N-ethylamino]pyridazin-3-carboxylic acid (185 mg, 0.46 mmol) was dissolved in dichloromethane (20 ml), (1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (EDAC), dimethylaminopyridine, (DMAP) (111 mg, 0.91 mmol) and propanesulfonamide (68 mg, 0.55 mmol) were added. The mixture was stirred at ambient temperature under argon overnight, after which TLC (25% water/CH3CN) suggested the reaction was complete. The reaction mixture was loaded directly onto a MPLC column (silica) and the title compound obtained by elution with 5% EtOH/CH2Cl2 then 5% EtOH/0.5% AcOH/CH2Cl2, as a clear oil which solidified on triturating with hexane to give a colourless powder (110 mg, 47%).
Sources & evidence
- ORD record
- ord-b9cf3959f96f4e03b2eb657f0673b830
- Source dataset
- uspto-grants-2000_08
- Patent number
- US06100258
Reaction notes
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