6-Amino-3-chloropyridazine → HCID 67173303, compound

HRID 552165Notes

Reaction equation

HRID 552165 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.Cl.[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[O:18])=[CH:13][CH:12]=1>CN1CCCC1=O>[NH2:8][C:5]1[N:6]=[N:7][C:2]([N:22]2[CH2:23][CH2:24][CH:19]([C:17]([C:14]3[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=3)=[O:18])[CH2:20][CH2:21]2)=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 216436-Amino-3-chloropyridazineHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochloride

Product 1

HCID 67173303HCID 67173303, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A stirred mixture of 6-chloropyridazin-3-ylamine (0.95 g, 7.28 mmol) and (4-fluorophenyl)piperidin-4-ylmethanone hydrochloride (3.22 g, 10.92 mmol) was heated at 150° C. in N-methylpyrrolidinone (125 mL) for 24 hours. The solvent was evaporated in vacuo and the residue was treated with 1 N NaOH solution and extracted with ethyl acetate. The organic layer was separated, dried over Na2SO4 and concentrated. The residue was purified by column chromatography to afford [1-(6-aminopyridazin-3-yl)piperidin-4-yl]-(4-fluorophenyl)methanone in 46% yield (1.00 g, 3.33 mmol).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionthe residue was treated with 1 N NaOH solution
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-36869888020d416285f8fcf30fe7a82c
Source dataset
uspto-grants-2011_05
Patent number
US07951805B2

Reaction notes

Loading…