Triethylamine → HCID 59716714, compound

HRID 2224210Notes

Reaction equation

HRID 2224210 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.[Cl:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C(N(CC)CC)C>N1C=CC=CC=1.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([N:15]2[C:14](=[O:17])[N:11]3[N:12]=[CH:13][C:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)=[C:9]([C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=4)[C:10]3=[N:16]2)=[CH:28][CH:27]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 742994-Chlorophenylboronic acidHCID 111641617,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

Product 1

HCID 59716714HCID 59716714, compoundYield 8%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a 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 and 4-chlorophenyboronic acid (44 mg, 0.28 mmol) in pyridine (1.5 mL) was added copper (II) acetate (51 mg, 0.28 mmol) followed by triethylamine (0.04 mL, 0.28 mmol) and 3 Å molecular sieves (100 mg) under argon. The reaction mixture was stirred at reflux for 6 h. After this time, the reaction mixture was cooled to RT and diluted with water (5 mL). The resultant mixture was extracted with EtOAc (3×5 mL). The combined organic layers were washed with water (2×5 mL) and saturated aqueous NaCl (2×5 mL). The organic layer was dried over MgSO4, filtered and concentrated to obtain a crude product. The crude product was purified by preparative HPLC to give 2,7,8-tris(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (5 mg, 8%) as yellow lyophilate. HPLC: 4.35 min; M+H=467; 1H NMR (CDCl3) δ 8.22 (1H, s), 8.10 (2H, d, J=10.0 Hz), 7.43 (2H, d, J=10.0 Hz), 7.35-7.38 (6H, m), 7.15 (2H, d, J=10.0 Hz).

Workup

  1. temperatureat reflux for 6 h
  2. extractionThe resultant mixture was extracted with EtOAc (3×5 mL)
  3. washThe combined organic layers were washed with water (2×5 mL) and saturated aqueous NaCl (2×5 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto obtain a crude product
  8. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-7e954d6a00364b7aa90fa78acd33b222
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

Loading…