Cesium carbonate → HCID 59716598, compound

HRID 2224208Notes

Reaction equation

HRID 2224208 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([O-])([O-])=O.[Cs+].[Cs+].Cl.Cl[CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>CN(C=O)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]([CH2:33][CH2:34][N:35]4[CH2:40][CH2:39][O:38][CH2:37][CH2:36]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

6

Reactant 3

HCID 10796Cesium carbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 111641617,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

Product 1

HCID 59716598HCID 59716598, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To 7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (40 mg, 0.11 mmol), prepared as described in Example 1, in DMF (1 mL) was added Cs2CO3 (110 mg, 0.33 mmol) and 4-(2-chloroethyl)morpholine hydrochloride (31 mg, 0.166 mmol). The reaction mixture was stirred at 70° C. for 30 min under argon. After this time, the reaction mixture was diluted with water (5 mL). The resulting solution was extracted with EtOAc (3×5 mL). The combined organic layers were washed with water (2×5 mL) and saturated aqueous sodium chloride (2×5 mL). The organic layer was concentrated. The resultant crude material was purified by preparative HPLC to give the title compound, 7,8-bis(4-chlorophenyl)-2-(2-morpholinoethyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (35 mg, 67%) as yellow solid. MS M+H=470; 1H NMR (CDCl3) δ 8.17 (1H, s), 7.28-7.34 (6H, m), 7.10 (2H, d, J=10.0 Hz), 4.44 (4H, t, J=5.0 Hz), 3.96-4.01 (4H), 3.50 (4H, t, J=5.0 Hz).

Workup

  1. extractionThe resulting solution was extracted with EtOAc (3×5 mL)
  2. washThe combined organic layers were washed with water (2×5 mL) and saturated aqueous sodium chloride (2×5 mL)
  3. concentrationThe organic layer was concentrated
  4. customThe resultant crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-e1d3b89e69d943a29ae8764f3311f6cc
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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