Potassium Carbonate → HCID 59716624, compound

HRID 2224229Notes

Reaction equation

HRID 2224229 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.[CH2:25]([O:29][CH2:30][CH3:31])[CH:26]1[O:28][CH2:27]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[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]([CH2:27][CH:26]([OH:28])[CH2:25][O:29][CH2:30][CH3:31])[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

6

Reactant 3

HCID 11430Potassium CarbonateHCID 19919Oxirane, 2-(ethoxymethyl)-HCID 111641617,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

Product 1

HCID 59716624HCID 59716624, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (300 mg, 0.84 mmol), prepared as described in Example 1, in 8 mL of DMF was added ethyl glycidyl ether (86 mg, 0.84 mmol), followed by K2CO3 (232 mg, 1.68 mmol). The mixture was heated at 85° C. After stirring overnight, the reaction was allowed to cool to RT The reaction mixture was diluted with EtOAc (200 mL). The resultant solution was washed with saturated aqueous NaCl (3×40 mL). The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified using silica gel column chromatography using an automated system, eluting with a gradient of 0% to 60% EtOAc/hexanes for 30 min followed by 100% EtOAc for 40 min. The title compound, 7,8-bis(4-chlorophenyl)-2-(3-ethoxy-2-hydroxypropyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (0.3 gm, 78% yield) as a yellow solid. MS [M+H]+: found 459; 1H NMR (CDCl3, 400 MHz) δ 8.20 (s, 1H), 7.34-7.25 (m, 6H), 7.09 (d, 2H), 4.29-4.24 (m, 2H), 4.18-4.13 (m, 1H), 3.57-3.49 (m, 4H), 1.17 (t, 3H).

Workup

  1. temperatureto cool to RT The reaction mixture
  2. washThe resultant solution was washed with saturated aqueous NaCl (3×40 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified
  7. washeluting with a gradient of 0% to 60% EtOAc/hexanes for 30 min
  8. waitfollowed by 100% EtOAc for 40 min

Sources & evidence

ORD record
ord-711e976434fd4e56835cd98562ae5297
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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