Hydrochloric Acid → HCID 135736617, compound

HRID 352909Notes

Reaction equation

HRID 352909 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:36])[C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)=[C:24]([O:34]C)[CH:23]=3)[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.O.C(=O)(O)[O-].[Na+].Cl>ClCCl.B(Br)(Br)Br.O1CCCC1.C(O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:36])[C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)=[C:24]([OH:34])[CH:23]=3)[CH2:17][CH2:16]1)(=[O:13])=[O:14])[CH:6]=[CH:5]2

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 22710029HCID 22710029, compound

Product 1

HCID 135736617HCID 135736617, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent3×HCID 8028TetrahydrofuranSolventHCID 25134Boron tribromideSolvent

Procedure

In dichloromethane (1 ml), boron tribromide (115 μl) was dissolved, followed by the dropwise addition of a solution of 1-[(6-chloronaphthalen-2-yl)sulfonyl]-4-[3-methoxy-4-(pyridin-4-yl)benzoyl]piperazine, which had been obtained in Example A-30, in dichloromethane (dichloromethane: 4 ml) at an external temperature of about −78° C. While heating gradually to room temperature, the resulting mixture was stirred for 23 hours. After dichloromethane and water were added to the reaction mixture and the resulting mixture was stirred for a while, sodium bicarbonate was added to make alkaline the reaction mixture, which was separated into an organic layer and a water layer. From the water layer, another organic layer was extracted with dichloromethane. These organic layers were combined together, washed with saturated aqueous NaCl solution and then dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (dichloromethane˜3% methanol—dichloromethane). The crudely purified product so obtained was dissolved in tetrahydrofuran. Solution of hydrochloride in ethanol was added to the resulting solution to solidify the same. The resulting solid was collected by filtration and then dissolved in a mixed solvent of water and methanol. After the removal of the insoluble matter by filtration, the filtrate was distilled under reduced pressure, whereby the title compound (36 mg, 30%) was obtained.

Workup

  1. additionwas added
  2. customwas separated into an organic layer
  3. extractionFrom the water layer, another organic layer was extracted with dichloromethane
  4. washwashed with saturated aqueous NaCl solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe residue obtained
  7. distillationby distilling off the solvent under reduced pressure
  8. customwas purified by chromatography on a silica gel column (dichloromethane˜3% methanol—dichloromethane)
  9. customThe crudely purified product so obtained
  10. filtrationThe resulting solid was collected by filtration
  11. dissolutiondissolved in a mixed solvent of water and methanol
  12. customAfter the removal of the insoluble matter
  13. filtrationby filtration
  14. distillationthe filtrate was distilled under reduced pressure, whereby the title compound (36 mg, 30%)
  15. customwas obtained

Sources & evidence

ORD record
ord-22cc0a020f524cfda069e36a8a118bc9
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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