HCID 58277355, compound → HCID 58277403, compound

HRID 1949214Notes

Reaction equation

HRID 1949214 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[N:18]=[C:17]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:16]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>C(O)(=O)C.[Pd]>[Cl:26][C:22]1[CH:21]=[C:20]([N:19]2[C:15]([C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[CH:10]=3)=[CH:16][C:17]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N:18]2)[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 1

HCID 58277355HCID 58277355, compound

Product 1

HCID 58277403HCID 58277403, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

19.1 g (44.1 mmol) of the compound of Example 43A are provided in 367 ml of conc. acetic acid, 23.5 g (11.0 mmol) of palladium on activated carbon (5%) are added, and the mixture is stirred under a hydrogen atmosphere at room temperature overnight. The reaction mixture is subsequently filtered, the filtrate is concentrated, the residue is taken up in dichloromethane and washed with an aqueous sodium bicarbonate solution, and the organic phase is dried over sodium sulfate and concentrated. 12.7 g of the title compound with 63% purity (53% of theory) are obtained.

Workup

  1. filtrationThe reaction mixture is subsequently filtered
  2. concentrationthe filtrate is concentrated
  3. washwashed with an aqueous sodium bicarbonate solution
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1b507b665854474cbfbe96005653bd37
Source dataset
uspto-grants-2013_03
Patent number
US08399682B2

Reaction notes

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