Potassium Carbonate → HCID 59716584, compound

HRID 2224223Notes

Reaction equation

HRID 2224223 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:14](=[O:17])[NH:15][N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.[C:25]1([N:31]2[C:35](Cl)=[N:34][N:33]=[N:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:14](=[O:17])[N:15]([C:35]4[N:31]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[N:32]=[N:33][N:34]=4)[N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 842621H-Tetrazole, 5-chloro-1-phenyl-HCID 111641617,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

Product 1

HCID 59716584HCID 59716584, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (50 mg, 0.14 mmol), prepared as described in Example 1, in 0.7 mL of DMF was added N-phenyl-5-chlorotetrazole (25 mg, 0.14 mmol) and 19 mg of K2CO3. The resulting red solution was heated at 80° C. for 4 days and, upon cooling to room temp, the mixture was diluted with 50 mL of ethyl acetate and 50 mL of 1N HCl. The layers were extracted, and the organic layer was washed with 50 mL of saturated aqueous NaCl. The organic layer was dried over MgSO4, filtered and evaporated to an orange solid. The material was purified via silica gel column chromatography followed by reverse phase HPLC to give the title compound, 7,8-bis(4-chlorophenyl)-2-(1-phenyl-1H-tetrazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (7 mg, 10%) yield as a yellow solid. LCMS Anal. Calc'd for C24H14Cl2N8O, 500.07, [M+H] 501 observed; 1H NMR (400 MHz, CD3CN) δ 8.30 (s, 1H), 7.69-7.55 (m, 5H), 7.39 (dt, 2H, J=2.1, 6.6 Hz), 7.28 (dt, 2H, J=1.9, 8.6 Hz), 7.23 (dt, 2H, J=2.2, 8.6 Hz), 7.06 (dt, 2H, J=2.1, 8.7 Hz).

Workup

  1. temperatureupon cooling to room temp
  2. extractionThe layers were extracted
  3. washthe organic layer was washed with 50 mL of saturated aqueous NaCl
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated to an orange solid
  7. customThe material was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-ff623a8408c44a5ca0ad95c641ac4c43
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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