2,4-Dichlorobenzylamine → N-(2,4-dichlorobenzyl)-3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carboxamide

HRID 970168Notes

Reaction equation

HRID 970168 reaction equation
CN(C)C=O.C(Cl)(=O)C(Cl)=O.[O:12]=[C:13]1[C:18]([C:19]([OH:21])=O)=[CH:17][C:16]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[N:15][NH:14]1.[Cl:28][C:29]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:30]=1[CH2:31][NH2:32]>ClCCl.C(N(CC)CC)C>[Cl:28][C:29]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:30]=1[CH2:31][NH:32][C:19]([C:18]1[C:13](=[O:12])[NH:14][N:15]=[C:16]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[CH:17]=1)=[O:21]

Participants

7

Reactant 4

HCID 14852,4-DichlorobenzylamineHCID 6228DimethylformamideHCID 65578Oxalyl chloride2×HCID 127902383-Oxo-6-(pyridin-4-yl)-2,3-dihydropyridazine-4-carboxylic acid

Product 1

HCID 10339420N-(2,4-dichlorobenzyl)-3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
19 °C

Procedure

0.02 cm3 of dimethylformamide and then 0.12 cm3 of oxalyl chloride were added to 0.3 g of 3-oxo-6-(pyridin-4-yl)-2,3-dihydropyridazine-4-carboxylic acid prepared as described in patent FR 2 481 284, dissolved in 10 cm3 of dichloromethane. The reaction medium was stirred for 3 hours at 19° C. A further 0.12 cm3 of oxalyl chloride was then added and the mixture was stirred for a further one hour at 19° C. The reaction mixture was then poured onto a solution of 10 cm3 of dichloromethane containing 0.19 cm3 of triethylamine and 0.21 cm3 of 2,4-dichlorobenzylamine. The reaction medium was stirred for 12 hours at 19° C. and then filtered through a sinter funnel, rinsed with 10 cm3 of dichloromethane, 10 cm3 of distilled water and with 10 cm3 of aqueous normal hydrochloric acid solution. After drying (10 kPa; 20° C.), 0.25 g of N-(2,4-dichlorobenzyl)-3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carboxamide was obtained in the form of a white solid melting at 233° C.

Workup

  1. customprepared
  2. stirringthe mixture was stirred for a further one hour at 19° C
  3. stirringThe reaction medium was stirred for 12 hours at 19° C.
  4. filtrationfiltered through a sinter funnel
  5. washrinsed with 10 cm3 of dichloromethane, 10 cm3 of distilled water and with 10 cm3 of aqueous normal hydrochloric acid solution
  6. customAfter drying (10 kPa; 20° C.)

Sources & evidence

ORD record
ord-e34a0e62334b455892da971a1391627f
Source dataset
uspto-grants-2007_12
Patent number
US07309701B2

Reaction notes

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