HCID 18176463, compound → HCID 18176452, compound

HRID 394448Notes

Reaction equation

HRID 394448 reaction equation
[CH2:1]([CH:8]1[NH:14][CH2:13][CH2:12][S:11][C:10]2[C:15](=[O:20])[N:16]([CH3:19])[N:17]=[CH:18][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I([O-])(=O)(=O)=[O:22].[Na+]>C(O)(=O)C.O>[CH2:1]([CH:8]1[NH:14][CH2:13][CH2:12][S:11](=[O:22])[C:10]2[C:15](=[O:20])[N:16]([CH3:19])[N:17]=[CH:18][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 18176463HCID 18176463, compoundHCID 23667635Sodium periodate

Product 1

HCID 18176452HCID 18176452, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 0.84 g (2.92 mmol) of 5-benzyl-8-methyl-2,3,4,5-tetrahydro-9(8H)-pyridazino[4,5-b][1,5]thiazepinone in 7.5 ml of glacial acetic acid the solution of 0.75 g (3.6 mmol) of sodium metaperiodate in 6 ml of water are added dropwise while stirring and cooling with ice-water. The reaction mixture is stirred for 3 hours while cooling with ice-water. The obtained suspension is filtered and washed with a small amount of water. The aqueous phase is extracted with 3×20 ml of dichloromethane. The organic phase is washed with 2×5 ml of 10% aqueous sodium carbonate solution and then with 2×10 ml of water. The organic phase is dried and evaporated in vacuum. The residue is crystallized from a 9:1 mixture of ethyl acetate and methanol. In this way 0.56 g (63%) of the title compound is obtained with a melting point of 162-163° C.

Workup

  1. stirringThe reaction mixture is stirred for 3 hours
  2. filtrationThe obtained suspension is filtered
  3. washwashed with a small amount of water
  4. extractionThe aqueous phase is extracted with 3×20 ml of dichloromethane
  5. washThe organic phase is washed with 2×5 ml of 10% aqueous sodium carbonate solution
  6. customThe organic phase is dried
  7. customevaporated in vacuum
  8. customThe residue is crystallized from a 9:1 mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-8e62ce59049e4cd2a8540f92757e5291
Source dataset
uspto-grants-2003_08
Patent number
US06602865B1

Reaction notes

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