Oxalyl chloride → N-[2-(2,4-dichlorophenyl)ethyl]-3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carboxamide

HRID 2374757Notes

Reaction equation

HRID 2374757 reaction equation
Cl[C:2]1[CH:24]=[C:23](Cl)[CH:22]=[CH:21][C:3]=1[CH2:4][NH:5][C:6]([C:8]1[C:9](=[O:20])[NH:10][N:11]=[C:12]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:13]=1)=[O:7].O=C1C(C(O)=O)=CC(C2C=CN=CC=2)=NN1.C(Cl)(=O)[C:43]([Cl:45])=O.[Cl:48]C(C1C=CC(Cl)=CC=1)CN>C(N(CC)CC)C.CN(C)C=O.ClCCl>[Cl:45][C:43]1[CH:2]=[C:24]([Cl:48])[CH:23]=[CH:22][C:21]=1[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:9](=[O:20])[NH:10][N:11]=[C:12]([C:14]2[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=2)[CH:13]=1)=[O:7]

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 10339420N-(2,4-dichlorobenzyl)-3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carboxamideHCID 107028222,4-DichlorophenylethylamineHCID 127902383-Oxo-6-(pyridin-4-yl)-2,3-dihydropyridazine-4-carboxylic acid

Product 1

HCID 10475428N-[2-(2,4-dichlorophenyl)ethyl]-3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carboxamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Working as in example 2 for the preparation of N-(2,4-dichlorobenzyl)-3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carboxamide, but starting with 0.3 g of 3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carboxylic acid, 10 cm3 of dichloromethane, 0.02 cm3 of dimethylformamide, 0.12 cm3 of oxalyl chloride, 0.23 cm3 of 2,4-dichlorophenylethylamine and 0.19 cm3 of triethylamine, 0.23 g of N-[2-(2,4-dichlorophenyl)ethyl]-3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carboxamide was obtained in the form of a cream-colored solid melting at 202° C.

Sources & evidence

ORD record
ord-a4e4489722414096a7462542f7ee2be3
Source dataset
uspto-grants-2008_12
Patent number
US07462613B2

Reaction notes

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