1,1'-Carbonyldiimidazole → 7-(4-chlorophenyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

HRID 2224241Notes

Reaction equation

HRID 2224241 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)=[C:22]([NH:26][NH2:27])[N:23]=[N:24][CH:25]=2)=[CH:16][CH:15]=1>C1COCC1>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:25]=[N:24][N:23]3[C:1](=[O:2])[NH:27][N:26]=[C:22]3[C:21]=2[C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 597169001-(5-(4-Chlorophenyl)-4-(pyridin-4-yl)pyridazin-3-yl)hydrazine

Product 1

HCID 597167437-(4-chlorophenyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-oneYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF (100 mL) solution of carbonyldiimidazole (CDI) (7.25 g, 44.71 mmol) was added 1-(5-(4-chlorophenyl)-4-(pyridin-4-yl)pyridazin-3-yl)hydrazine (3.8 g, 12.76 mmol) portionwise at RT under an atmosphere of argon. The reaction mixture was heated to reflux for 30 min. After this time, the reaction mixture was cooled to RT, and subsequently concentrated under reduced pressure to obtain a gum to which water (100 mL) was added. The resulting solid was collected by filtration, washed with water (2×50 mL) followed by 1:1 (v/v) of hexanes/ether (2×50 mL) to give the title compound, 7-(4-chlorophenyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (3.75 g, 91%) as yellow solid. HPLC: 1.67 min; MS, M+H=324; 1H NMR (DMSO-d6) δ 12.90 (1H, s), 8.59 (2H, d, J=10.0 Hz), 8.41 (1H, s), 7.44 (2H, d, J=10.0 Hz), 7.32 (2H, d, J=5.0 Hz), 7.28 (2H, d, J=5.0 Hz).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 30 min
  3. concentrationsubsequently concentrated under reduced pressure
  4. customto obtain a gum to which water (100 mL)
  5. additionwas added
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with water (2×50 mL)

Sources & evidence

ORD record
ord-4d9c00d054ea46bf90e2e03d2c11cfb1
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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