Ethyl bromoacetate → ethyl (R)-2-{1-[1-(acenaphthen-1-yl)piperidin-4-yl]-1,2-dihydro-2-oxo-imidazo[4,5-b]pyridin-3-yl}acetate

HRID 331250Notes

Reaction equation

HRID 331250 reaction equation
[C@H:1]1([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[NH:21][C:20]3=[O:28])[CH2:15][CH2:14]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1.[H-].[Na+].Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>CN(C=O)C>[C@H:1]1([N:13]2[CH2:14][CH2:15][CH:16]([N:19]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[N:21]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:20]3=[O:28])[CH2:17][CH2:18]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 59322973HCID 59322973, compound

Product 1

HCID 86641636ethyl (R)-2-{1-[1-(acenaphthen-1-yl)piperidin-4-yl]-1,2-dihydro-2-oxo-imidazo[4,5-b]pyridin-3-yl}acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-1-[1-(Acenaphthen-1-yl)piperidin-4-yl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1 g) was dissolved in DMF (30 ml). Sodium hydride (120 mg, 60%) was added, and the suspension was stirred at room temperature for 20 min. Ethyl bromoacetate (500 mg) was added, and the mixture was stirred for 2 hr. The reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated aqueous ammonium chloride solution, dried over magnesium sulfate, and concentration to give ethyl (R)-2-{1-[1-(acenaphthen-1-yl)piperidin-4-yl]-1,2-dihydro-2-oxo-imidazo[4,5-b]pyridin-3-yl}acetate. 40% Methylamine-methanol solution (20 ml) was added, the mixture was stirred at room temperature for 2 hr, and the reaction mixture was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to give the title compound (0.86 g) as a white powder.

Workup

  1. stirringthe mixture was stirred for 2 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated aqueous ammonium chloride solution
  4. dry with materialdried over magnesium sulfate, and concentration

Sources & evidence

ORD record
ord-ef0927b04be743e6ad09c4e798267217
Source dataset
uspto-grants-2014_11
Patent number
US08877779B2

Reaction notes

Loading…