Triethylamine → HCID 178477817, compound

HRID 2205791Notes

Reaction equation

HRID 2205791 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][N:5]=[C:4]2[NH:14][N:15]=[CH:16][C:3]=12.[Br:17]Br.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:17][C:16]1[C:3]2[C:4](=[N:5][N:6]=[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:2]=2[Cl:1])[NH:14][N:15]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 24408Bromine3×HCID 516892Sodium BicarbonateHCID 867172634-chloro-5-phenyl-1H-pyrazolo[3,4-c]pyridazine

Product 1

HCID 178477817HCID 178477817, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-chloro-5-phenyl-1H-pyrazolo[3,4-c]pyridazine (155 mg, 0.67 mmol), bromine (51 μL, 1 mmol) and triethylamine (98 μL, 0.7 mmol) in chloroform (4 mL) was stirred at room temperature for 1 h. Additional bromine (25 μL) and chloroform (4 mL) were added and the reaction mixture was stirred at room temperature for 4 h. Further bromine (25 μL) and triethylamine (98 μL) were added and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with CH2Cl2 and a sodium bicarbonate solution. The aqueous phase was extracted with CH2Cl2 and the combined organic phases were dried (phase separator cartridge) and concentrated in vacuo. The resultant residue was purified using chromatography (silica gel, ethyl acetate/isohexane 0:1 to 1:1), to provide Compound Ibb as a solid (97 mg).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 4 h
  2. stirringthe reaction mixture was stirred at room temperature for 16 h
  3. extractionThe aqueous phase was extracted with CH2Cl2
  4. customthe combined organic phases were dried (phase separator cartridge)
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified

Sources & evidence

ORD record
ord-e66ee6b1e21146aea990f824d4b4f505
Source dataset
uspto-grants-2016_06
Patent number
US09371332B2

Reaction notes

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