2-Dimethylaminopyridine → N-Propyl-6-(N-[5-bromo-2-propoxybenzyl]-N-ethylamino)pyridazine-3-carboxamide

HRID 840292Notes

Reaction equation

HRID 840292 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH2:22][CH2:23][CH3:24])=[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].C[N:26]([C:28]1[CH:33]=[CH:32]C=CN=1)C.C(S(N)(=O)=O)CC.CO.ClCCl>ClCCl.CN(C1C=CN=CC=1)C>[CH2:28]([NH:26][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][CH2:23][CH3:24])[CH2:9][CH3:10])=[CH:12][CH:13]=1)=[O:19])[CH2:33][CH3:32]

Participants

7

Reactant 4

HCID 218852-DimethylaminopyridineHCID 3401849Propane-1-sulphonamideHCID 21226129Dichloromethane methanol2×HCID 22622530HCID 22622530, compound

Product 1

HCID 22622553N-Propyl-6-(N-[5-bromo-2-propoxybenzyl]-N-ethylamino)pyridazine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

6-(N-[5-Bromo-2-propoxybenzyl]-N-ethylamino)pyridazine-3-carboxylic acid (example 18)-(500 mg, 1.27 mmol) was dissolved in dichloromethane (50 ml), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (EDAC),(365mg, 2.07 mmol), dimethylaminopyridine, (DMAP) (465 mg, 3.81 mmol) and propanesulfonamide (190 mg, 1.54 mmol) was added. The mixture was stirred at ambient temperature under argon overnight, after which TLC (5% methanol/dichloromethane) suggested the reaction was complete. The reaction mixture was loaded directly onto a MPLC column (silica) and the title compound obtained by elution 5% methanol/dichloromethane as a foam (380 mg, 60%).

Sources & evidence

ORD record
ord-e3b86b755f31424596218593e2369837
Source dataset
uspto-grants-2002_04
Patent number
US06365603B1

Reaction notes

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