HCID 59351234, compound → HCID 59351206, compound

HRID 887488Notes

Reaction equation

HRID 887488 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:32]=[CH:31][C:15]([O:16][C:17]2[C:18]([C:23]3[CH2:28][CH2:27][N:26]([CH3:29])[C:25](=[O:30])[CH:24]=3)=[N:19][CH:20]=[CH:21][N:22]=2)=[CH:14][CH:13]=1)=[O:11]>[Pd].CCO.O1CCOCC1>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:13]=[CH:14][C:15]([O:16][C:17]2[C:18]([CH:23]3[CH2:28][CH2:27][N:26]([CH3:29])[C:25](=[O:30])[CH2:24]3)=[N:19][CH:20]=[CH:21][N:22]=2)=[CH:31][CH:32]=1)=[O:11]

Participants

4

Reactant 1

HCID 59351234HCID 59351234, compound

Product 1

HCID 59351206HCID 59351206, compoundYield 38.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22560076Dioxan ethanolSolvent

Procedure

A solution of 4-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)-1-methyl-5,6-dihydropyridin-2(1H)-one (0.0687 g, 0.161 mmol) (Step 7, Example 252) in 1:1 EtOH-dioxane (8 mL) was added palladium, 10% wt. on activated carbon (0.007 g, 6.58 μmol) and hydrogenated (double-walled balloon pressure) at room temperature for 24 h. The reaction mixture was filtered via a pad of Celite, and the filtrate was concentrated in vacuo and purified via flash column chromatography (20% to 80% EtOAc (10% MeOH)/Hexanes) to give 4-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)-1-methylpiperidin-2-one (0.0262 g, 38.0% yield) as a light yellow amorphous solid. MS (ESI, pos. ion) m/z: 428.9 (M+1). IC50 (uM) +++++.

Workup

  1. filtrationThe reaction mixture was filtered via a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. custompurified via flash column chromatography (20% to 80% EtOAc (10% MeOH)/Hexanes)

Sources & evidence

ORD record
ord-8503ebfc40bb4e62bec432339ab9c07b
Source dataset
uspto-grants-2012_08
Patent number
US08247418B2

Reaction notes

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