HCID 178527162, compound → HCID 178527160, compound

HRID 1767649Notes

Reaction equation

HRID 1767649 reaction equation
Cl[C:2]1[C:7]2[N:8]=[C:9]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[NH:10][S:11](=[O:13])(=[O:12])[C:6]=2[C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:4][CH:3]=1>CCO.[Pd]>[CH:14]1([C:9]2[NH:10][S:11](=[O:12])(=[O:13])[C:6]3[C:5]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)=[CH:4][CH:3]=[CH:2][C:7]=3[N:8]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

4

Reactant 1

HCID 178527162HCID 178527162, compound

Product 1

HCID 178527160HCID 178527160, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-chloro-3-cyclohexyl-8-(2-pyridyl)-1,2-dihydro-1,2,4-benzothiadiazine-1,1-dioxide (0.268 g, 0.713 mmol) was dissolved in 99% EtOH (50 ml) and hydrogenated using Pd/C (10%, 10 mg) at 4 bar pressure for 24 h. The mixture was filtered through a pad of Celite™ and the solvent was removed under reduced pressure. The residue was dissolved in EtOAc (50 ml) and washed with phosphate buffer (pH=7, 10 ml), dried (Na2SO4) and the solvent was removed under reduced pressure, yielding 200 mg (82%) of 3-cyclohexyl-8-(2-pyridyl)-1,2-dihydro-1,2,4-benzothiadiazine-1,1-dioxide as colorless crystals. The product was further transformed by Method F. M.p. 200–203° C.

Workup

  1. customfor 24 h
  2. filtrationThe mixture was filtered through a pad of Celite™
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in EtOAc (50 ml)
  5. washwashed with phosphate buffer (pH=7, 10 ml)
  6. dry with materialdried (Na2SO4)
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-860614f2528e4511a24e37ec4c7ce958
Source dataset
uspto-grants-2007_06
Patent number
US07235548B2

Reaction notes

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