Acetonitrile → HCID 89690348, compound

HRID 2202893Notes

Reaction equation

HRID 2202893 reaction equation
[OH:1][C:2]1[CH:7]=[N:6][N:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][O:9]2)[C:4](=[O:14])[CH:3]=1.Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1.CC#N.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][O:1][C:2]2[CH:7]=[N:6][N:5]([CH:8]3[CH2:13][CH2:12][CH2:11][CH2:10][O:9]3)[C:4](=[O:14])[CH:3]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 579503555-Hydroxy-2-(2-tetrahydropyranyl)pyridazin-3(2H)-one

Product 1

HCID 89690348HCID 89690348, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-hydroxy-2-(tetrahydro-2H-pyran-2-yl)pyridazin-3(2H)-one (200 mg), 1-bromomethyl-4-chlorobenzene (209 mg), CH3CN (8 ml) and DMF (1 ml) was added potassium carbonate (282 mg), and the resulting mixture was stirred at room temperature for 16 h. The reaction mixture was then concentrated in vacuo and diluted with water. The mixture was extracted with EtOAc, and extract was washed successively with water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was triturated with n-hexane to give the title compound (210 mg) as a white solid.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. additiondiluted with water
  3. extractionThe mixture was extracted with EtOAc
  4. extractionextract
  5. washwas washed successively with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-69ce72524f1e422ba9fd93757aef825b
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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