HCID 67572480, compound → HCID 67642996, compound

HRID 1956696Notes

Reaction equation

HRID 1956696 reaction equation
[C:1]([C:3]1[CH:43]=[CH:42][C:6]([CH2:7][N:8]2[C:12]([CH2:13][NH:14][C@@H:15]([CH2:36][CH2:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH2:16][N:17](C(OCC3C=CC=CC=3)=O)[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].[H][H]>CO.CCOC(C)=O.[Pd]>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]([CH2:13][NH:14][C@@H:15]([CH2:36][CH2:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH2:16][NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)=[CH:11][N:10]=[CH:9]2)=[CH:42][CH:43]=1)#[N:2]

Participants

6

Reactant 2

HCID 67572480HCID 67572480, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67642996HCID 67642996, compoundYield 49.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product from Step F (163 mg, 0.262 mmol) in 3 mL of methanol and 3 mL of EtOAc was added at room temperature 10% palladium on carbon (10 mg). A balloon of hydrogen gas was introduced to the solution via syringe needle, and the reaction was stirred for ca. 20 minutes. The solution was filtered through celite to remove the catalyst, then concentrated in vacuo. The resulting product was purified by silica gel chromatography (4% MeOH/CH2Cl2 with 1% NH4OH) to provide the titled compound (63 mg).

Workup

  1. filtrationThe solution was filtered through celite
  2. customto remove the catalyst
  3. concentrationconcentrated in vacuo
  4. customThe resulting product was purified by silica gel chromatography (4% MeOH/CH2Cl2 with 1% NH4OH)

Sources & evidence

ORD record
ord-2691fd7c5eff4a56a740a4148409bad2
Source dataset
uspto-grants-1998_07
Patent number
US05780492

Reaction notes

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