Potassium Carbonate → HCID 178429566, compound

HRID 1073136Notes

Reaction equation

HRID 1073136 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:14]([CH3:20])[CH2:15][C:16](=[O:19])[NH:17][N:18]=3)=[CH:9][C:8]=2[N+:21]([O-:23])=[O:22])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:24](C1NC=CN=1)(C1NC=CN=1)=[O:25].[NH:36]1[CH:40]=[C:39]([CH2:41][CH2:42][CH2:43][NH2:44])[N:38]=[CH:37]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH:36]1[CH:40]=[C:39]([CH2:41][CH2:42][CH2:43][NH:44][C:24]([N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:12]=[CH:11][C:10]([C:13]4[CH:14]([CH3:20])[CH2:15][C:16](=[O:19])[NH:17][N:18]=4)=[CH:9][C:8]=3[N+:21]([O-:23])=[O:22])[CH2:2][CH2:3]2)=[O:25])[N:38]=[CH:37]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 14459461HCID 14459461, compoundHCID 178510931HCID 178510931, compound

Product 1

HCID 178429566HCID 178429566, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

3.0 g (9.5 mmol) of 6-[4-(1-Piperazinyl)-3-nitro-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone and 1.7 g (10.5 mmol) of carbonyl diimidazole are stirred together in 30 ml of DMF at room temperature for 2 hours. 1.88 g (15 mmol) of 3-(1H-imidazol-4-yl)-propylamine are then added and the reaction mixture is heated to 70° C. for 8 hours. After cooling, 10 ml of a saturated aqueous potassium carbonate solution are added and the reaction mixture is extracted with chloroform. The organic phase is concentrated by evaporation under vacuum and the residue is chromatographed on silica gel (Solvent F). Concentration of the main fractions by evaporation and crystallization of the residue yields 2.3 g (52% of theoretical) of orange crystals which have a melting point of 182° C.

Workup

  1. temperatureAfter cooling
  2. extractionthe reaction mixture is extracted with chloroform
  3. concentrationThe organic phase is concentrated by evaporation under vacuum
  4. customthe residue is chromatographed on silica gel (Solvent F)
  5. customConcentration of the main fractions by evaporation and crystallization of the residue
  6. customyields 2.3 g (52% of theoretical) of orange crystals which

Sources & evidence

ORD record
ord-7fd47801a3054cc885841f3515f22854
Source dataset
uspto-grants-1990_11
Patent number
US04968683

Reaction notes

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