Isonicotinic Acid → HCID 13715243, compound

HRID 1650155Notes

Reaction equation

HRID 1650155 reaction equation
[C:1](O)(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH3:10][CH:11]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][CH3:24])=[C:19]([NH2:25])[CH:18]=2)=[N:15][NH:14][C:13](=[O:26])[CH2:12]1.C1COCC1>C(O)(=O)C>[CH3:10][CH:11]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]3[N:23]([CH3:24])[C:1]([C:2]4[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=4)=[N:25][C:19]=3[CH:18]=2)=[N:15][NH:14][C:13](=[O:26])[CH2:12]1

Participants

5

Reactant 3

HCID 5922Isonicotinic AcidHCID 8028TetrahydrofuranHCID 22167831HCID 22167831, compound

Product 1

HCID 13715243HCID 13715243, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 12.3 g of isonicotinic acid, 23.2 g of 5-methyl-6-(3-amino-4-methylaminophenyl)-4,5-dihydropyridazin-3-one, 16.2 g of N,N'-carbonyldiimidazole and 600 ml of THF is stirred at 25° for 16 hours. After the usual working up, an oily mixture of 5-methyl-6-(3-amino-4-N-methylisonicotinamidophenyl)- and 5-methyl-6-(3-isonicotinamido-4-methylaminophenyl)-4,5-dihydropyridazin-3-one is obtained and is dissolved in 400 ml of acetic acid. After the solution has been boiled for 3 hours, then cooled and submitted to the usual working up, 5-methyl-6-[1-methyl-2-(4-pyridyl)-5-benzimidazolyl]-4,5-dihydropyridazin-3-one is obtained; dihydrochloride, decomposition above 298°.

Workup

  1. customis obtained
  2. waitAfter the solution has been boiled for 3 hours
  3. temperaturecooled

Sources & evidence

ORD record
ord-c3f44270022b447b980089edaef42846
Source dataset
uspto-grants-1990_05
Patent number
US04923869

Reaction notes

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