Diethyl Malonate → Ethyl 7-(4-methoxybenzyl)-1-methyl-2,8-dioxo-1,2,7,8-tetrahydropyrido[2,3-d]pyridazine-3-carboxylate

HRID 1966383Notes

Reaction equation

HRID 1966383 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[C:13](=[O:14])[C:12]([NH:15][CH3:16])=[C:11]([CH:17]=O)[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[C:21]([O:29][CH2:30][CH3:31])(=[O:28])[CH2:22][C:23]([O:25]CC)=O.N1CCCCC1>CCO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:13](=[O:14])[C:12]3[N:15]([CH3:16])[C:23](=[O:25])[C:22]([C:21]([O:29][CH2:30][CH3:31])=[O:28])=[CH:17][C:11]=3[CH:10]=[N:9]2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 8082PiperidineHCID 469305321-(4-Methoxybenzyl)-5-(methylamino)-6-oxo-1,6-dihydropyridazine-4-carbaldehyde

Product 1

HCID 46930534Ethyl 7-(4-methoxybenzyl)-1-methyl-2,8-dioxo-1,2,7,8-tetrahydropyrido[2,3-d]pyridazine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(4-methoxybenzyl)-5-(methylamino)-6-oxo-1,6-dihydropyridazine-4-carbaldehyde (4) (3.78 g, 13.8 mmol), diethyl malonate (4.20 mL, 27.7 mmol), piperidine (1.44 mL, 14.5 mmol), and EtOH (100 mL) was stirred at reflux in an oil bath for 5 h. The reaction mixture was allowed to stand at RT for 18 h to afford a suspension. The solid was collected by suction filtration, washed with EtOH (10 mL), and dried in vacuo to afford ethyl 7-(4-methoxybenzyl)-1-methyl-2,8-dioxo-1,2,7,8-tetrahydropyrido[2,3-d]pyridazine-3-carboxylate as a tan solid. MS (ESI, pos. ion) m/z: 370 (M+1).

Workup

  1. temperatureat reflux in an oil bath for 5 h
  2. customto afford a suspension
  3. filtrationThe solid was collected by suction filtration
  4. washwashed with EtOH (10 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a8fb2e38445a4c02be49f43245e10541
Source dataset
uspto-grants-2013_04
Patent number
US08420649B2

Reaction notes

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