Thionyl Chloride → HCID 86700713, compound

HRID 925305Notes

Reaction equation

HRID 925305 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[N:11]=[N:10][C:9]([C:12]([OH:14])=O)=[CH:8][CH:7]=1.Cl.[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]2[CH2:26][CH2:27][NH2:28].C(N(C(C)C)C(C)C)C>C(Cl)(Cl)Cl.ClCCl>[Cl:5][C:6]1[N:11]=[N:10][C:9]([C:12]([NH:28][CH2:27][CH2:26][C:20]2[C:19]3[C:23](=[CH:24][CH:25]=[C:17]([Cl:16])[CH:18]=3)[NH:22][CH:21]=2)=[O:14])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 64157626-chloropyridazine-3-carboxylic Acid

Product 1

HCID 86700713HCID 86700713, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.092 mL; 0.150 mmol) was added to a suspension of 6-chloropyridazine-3-carboxylic acid (0.100 g; 0.630 mmol) in chloroform (1 mL); the resulting mixture was refluxed for 18 hours and concentrated under reduced pressure. The residue was dissolved in dichloromethane (3 mL) and 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.160 g; 0.693 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.271 mL; 1.58 mmol) were added. The resulting green solution was stirred at room temperature for 2 hours, diluted with dichloromethane and successively washed with sodium hydrogen sulphate (1M), sodium carbonate (1M) and brine, dried over magnesium sulphate and the crude material was purified by flash chromatography on silica gel (eluent 10 to 60% ethyl acetate in dichloromethane) to yield 0.048 g (23%) of 6-chloro-N-(2-(5-chloro-1H-indol-3-yl)ethyl)pyridazine-3-carboxamide.

Workup

  1. temperaturethe resulting mixture was refluxed for 18 hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane (3 mL)
  4. washsuccessively washed with sodium hydrogen sulphate (1M), sodium carbonate (1M) and brine
  5. dry with materialdried over magnesium sulphate
  6. customthe crude material was purified by flash chromatography on silica gel (eluent 10 to 60% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-deba251a0c204287b14f9ef303cd4361
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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