2,4-Dichlorobenzylamine → HCID 10022320, compound

HRID 2374780Notes

Reaction equation

HRID 2374780 reaction equation
[Cl:1][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=C[CH:15]=2)[CH:13]=1)=[O:7].O=[C:27]1C(C(O)=O)=CC(C2C=NC=CC=2)=N[NH:28]1.C(Cl)(=O)C(Cl)=O.ClC1C=C(Cl)C=CC=1CN>C(N(CC)CC)C.CN(C)C=O.ClCCl>[Cl:1][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:15]=[N:28][CH:27]=[CH:18][CH:19]=2)[CH:13]=1)=[O:7]

Participants

8

Reactant 4

HCID 14852,4-DichlorobenzylamineHCID 65578Oxalyl chlorideHCID 10339420N-(2,4-dichlorobenzyl)-3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carboxamideHCID 20527846HCID 20527846, compound

Product 1

HCID 10022320HCID 10022320, compound

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-3-yl-2,3-dihydropyridazine-4-carboxylic acid, 10 cm3 of dichloromethane, 1 cm3 of dimethylformamide, 0.12 cm3 of oxalyl chloride, 0.21 cm3 of 2,4-dichlorobenzylamine and 0.22 cm3 of triethylamine, and after purification by chromatography on silica gel (particle size 40-63 μm, under an argon pressure of 150 kPa), eluting with a mixture of dichloromethane and methanol (90/10 by volume), 0.204 g of N-(2,4-dichlorobenzyl)-3-oxo-6-pyridin-3-yl-2,3-dihydropyridazine-4-carboxamide was obtained in the form of a cream-colored solid melting at a temperature in the region of 260° C.

Workup

  1. customafter purification by chromatography on silica gel (particle size 40-63 μm
  2. washunder an argon pressure of 150 kPa), eluting with a mixture of dichloromethane and methanol (90/10 by volume)

Sources & evidence

ORD record
ord-8940b950904d4fa98e39a04d9c9855e2
Source dataset
uspto-grants-2008_12
Patent number
US07462613B2

Reaction notes

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