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

HRID 1604358Notes

Reaction equation

HRID 1604358 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 226225306-(N-[5-Bromo-2-propoxybenzyl]-N-ethylamino)pyridazine-3-carboxylic Acid

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-propoxvbenzyl]-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),(365 mg, 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-8c2742c6b5b045d9bdbbf1fe87da9046
Source dataset
uspto-grants-1999_11
Patent number
US05994353

Reaction notes

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