Pyridine → 2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-[3-(4-methyl-1-piperazinyl)propyl]-2H-pyridazin-3-one

HRID 985030Notes

Reaction equation

HRID 985030 reaction equation
[CH:1]1([N:4]2[C:9](=O)[C:8](CO)=C(C)C(C3C=CC(OC)=C(F)C=3)=N2)[CH2:3]C1.Br[CH2:24][C:25]1[C:26](=[O:44])[N:27]([CH2:40][CH:41]2[CH2:43][CH2:42]2)[N:28]=[C:29]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([F:39])[CH:32]=2)[CH:30]=1.C(Br)(Br)(Br)Br.[N:50]1C=CC=C[CH:51]=1.[C:56]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:57]=1>O1CCCC1>[CH:41]1([CH2:40][N:27]2[C:26](=[O:44])[C:25]([CH2:24][CH2:56][CH2:57][N:4]3[CH2:1][CH2:3][N:50]([CH3:51])[CH2:8][CH2:9]3)=[CH:30][C:29]([C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([F:39])[CH:32]=3)=[N:28]2)[CH2:43][CH2:42]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 69804695HCID 69804695, compound

Product 1

HCID 101365362-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-[3-(4-methyl-1-piperazinyl)propyl]-2H-pyridazin-3-oneYield 69.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Preparation of 4-bromomethyl-2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one 2-Cyclopropyl-methyl-6-(3-fluoro-4-methoxyphenyl)-4-hydroxymethyl-2H-pyridazin-3-one (185 mg, 0.61 mmol), carbon tetrabromide (404 mg, 1.2 mmol) and pyridine (48 mg, 0.61 mmol) were dissolved in tetrahydrofuran (3 mL), and under ice-cold stirring, a solution of triphenylphosphine (319 mg, 1.2 mmol) in tetrahydrofuran (3 mL) was added. Under ice cooling, the mixture was stirred for 1 hour, and further stirred overnight at room temperature. Insoluble materials were filtered off, the solvent was distilled off under reduced pressure, and the residue was isolated and purified by column chromatography on silica gel (hexane/ethyl acetate=2/1) to yield the title compound as a yellow powder (yield: 155 mg, 69.5%).

Workup

  1. customfurther stirred overnight
  2. customat room temperature
  3. filtrationInsoluble materials were filtered off
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe residue was isolated
  6. custompurified by column chromatography on silica gel (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-1e51c28f46eb4ba8bcfa71054cdb1774
Source dataset
uspto-grants-2005_03
Patent number
US06869954B2

Reaction notes

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