HCID 131725199, compound → HCID 22285667, compound

HRID 1062468Notes

Reaction equation

HRID 1062468 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([Cl:25])[C:15]=1[O:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[CH:5]=[C:6]1[S:10][C:9](=[O:11])[NH:8][C:7]1=[O:12].[H][H]>C(OCC)(=O)C.CO.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([Cl:25])[C:15]=1[O:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1)[CH2:5][CH:6]1[S:10][C:9](=[O:11])[NH:8][C:7]1=[O:12]

Participants

5

Reactant 2

HCID 131725199HCID 131725199, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22285667HCID 22285667, compoundYield 55.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

The title compound of Step C (93 mg) was dissolved in ethyl acetate/methanol (4 ml/2 ml) and then 10% palladium on carbon (70 mg) was added. The reaction mixture was placed on Parr shaker for four hours under 50 psi hydrogen at room temperature. The solution was filtered through diatomaceous earth, and concentrated. The residue was purified by preparative TLC (3% methanol in dichloromethane) to afford the title compound (52 mg) as a solid. MS (APCI−) Calc: 397.0, Found: 396.0 (M−1).

Workup

  1. filtrationThe solution was filtered through diatomaceous earth
  2. concentrationconcentrated
  3. customThe residue was purified by preparative TLC (3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-3360918e40204523a71c23cd90e3f363
Source dataset
uspto-grants-2005_11
Patent number
US06960604B2

Reaction notes

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