Oxalyl chloride → N-(4-chlorobenzyl)-3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carboxamide

HRID 970170Notes

Reaction equation

HRID 970170 reaction equation
Cl[C:2]1[CH:24]=[C:23]([Cl:25])[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(Cl)=O.ClC1C=CC(CN)=CC=1>C(N(CC)CC)C.CN(C)C=O.ClCCl>[Cl:25][C:23]1[CH:24]=[CH:2][C:3]([CH2:4][NH:5][C:6]([C:8]2[C:9](=[O:20])[NH:10][N:11]=[C:12]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[CH:13]=2)=[O:7])=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 660364-ChlorobenzylamineHCID 10339420N-(2,4-dichlorobenzyl)-3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carboxamideHCID 127902383-Oxo-6-(pyridin-4-yl)-2,3-dihydropyridazine-4-carboxylic acid

Product 1

HCID 10382654N-(4-chlorobenzyl)-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, 0.19 cm3 of 4-chlorobenzylamine and 0.19 cm3 of triethylamine, 0.2 g of N-(4-chlorobenzyl)-3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carboxamide was obtained in the form of a cream-colored solid melting at 250° C.

Sources & evidence

ORD record
ord-767657091dd24e7eba41febfa76620f6
Source dataset
uspto-grants-2007_12
Patent number
US07309701B2

Reaction notes

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