Water → HCID 19016833, compound

HRID 1728941Notes

Reaction equation

HRID 1728941 reaction equation
[C:1]([O:4][CH2:5][C:6]([C:8]1[S:29][C:11]2[S:12][CH2:13][CH2:14][C:15]3[C:16](=[N:17][N:18]([C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=4)[C:19](=[O:21])[CH:20]=3)[C:10]=2[CH:9]=1)=O)(=[O:3])[CH3:2].C([SiH](CC)CC)C.O>FC(F)(F)C(O)=O>[C:1]([O:4][CH2:5][CH2:6][C:8]1[S:29][C:11]2[S:12][CH2:13][CH2:14][C:15]3[C:16](=[N:17][N:18]([C:22]4[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=4)[C:19](=[O:21])[CH:20]=3)[C:10]=2[CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 12052TriethylsilaneHCID 19016811HCID 19016811, compound

Product 1

HCID 19016833HCID 19016833, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 2.8 g of 9-acetyloxyacetyl-2-(4-chlorophenyl)-5,6-dihydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one obtained in Example 51 in 40 ml of trifluoroacetic acid is added 3.0 ml of triethylsilane and the mixture is stirred for 5 hours at room temperature. After the completion of reaction, to the mixture is added water and the solution is extracted with chloroform. The extract is washed, dried and concentrated under reduced pressure. The resulting residue is subjected to column chromatography on silica gel and eluted with a mixed solvent of chloroform and methanol (99:1). The crystals obtained from the fraction are recrystallized from a mixed solvent of chloroform and ethanol to give 1.0 g of 9-(2-acetoxyethyl)-2-(4-chlorophenyl)-5,6-dihydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one as white crystals, melting at 115°-117° C.

Workup

  1. customAfter the completion of reaction
  2. extractionthe solution is extracted with chloroform
  3. washThe extract is washed
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. washeluted with a mixed solvent of chloroform and methanol (99:1)
  7. customThe crystals obtained from the fraction
  8. customare recrystallized from a mixed solvent of chloroform and ethanol

Sources & evidence

ORD record
ord-dfe7467bc731454293f3a05e1b728b17
Source dataset
uspto-grants-1994_07
Patent number
US05329016

Reaction notes

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