Thionyl Chloride → HCID 58585284, compound

HRID 2252292Notes

Reaction equation

HRID 2252292 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]([O:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)=[CH:18][CH:17]=3)=[C:11]([N:29]3[CH2:34][CH2:33][CH:32](O)[CH2:31][CH2:30]3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.S(Cl)([Cl:38])=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13](=[O:14])[C:12]([O:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=4)=[CH:18][CH:17]=3)=[C:11]([N:29]3[CH2:34][CH2:33][CH:32]([Cl:38])[CH2:31][CH2:30]3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 69139123HCID 69139123, compound

Product 1

HCID 58585284HCID 58585284, compound

Procedure

A suspension of 150 mg (0.305 mmol) of 2-(4-chlorophenyl)-4-(4′-fluorobiphenyl-4-yloxy)-5-(4-hydroxypiperidin-1-yl)-2H-pyridazin-3-one (obtainable in analogy to Example 15) is heated under reflux with 4 ml of thionyl chloride for 60 min. After cooling, the reaction solution is concentrated under high vacuum, the residue is partitioned between 50 ml of ethyl acetate and 20 ml of saturated sodium bicarbonate solution, the organic phase is separated off, and the aqueous phase is extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulfate, and the solvent is removed in vacuo. The product is purified by chromatography on silica gel with toluene/ethyl acetate from 9:1 to 8:2 as mobile phase.

Workup

  1. temperatureis heated
  2. temperatureAfter cooling
  3. concentrationthe reaction solution is concentrated under high vacuum
  4. customthe residue is partitioned between 50 ml of ethyl acetate and 20 ml of saturated sodium bicarbonate solution
  5. customthe organic phase is separated off
  6. extractionthe aqueous phase is extracted three times with ethyl acetate
  7. dry with materialThe combined organic phases are dried over sodium sulfate
  8. customthe solvent is removed in vacuo
  9. customThe product is purified by chromatography on silica gel with toluene/ethyl acetate from 9:1 to 8:2 as mobile phase

Sources & evidence

ORD record
ord-fadeffca5fbb48579614784d8f45dd80
Source dataset
uspto-grants-2008_01
Patent number
US07320977B2

Reaction notes

Loading…