Sodium hydride → HCID 57612825, compound

HRID 1668427Notes

Reaction equation

HRID 1668427 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11](=[O:27])[NH:12][C:13]1[C:14](=[O:26])[NH:15][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])=[CH:17][CH:18]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH2:29][C:30]([NH:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:31]>CN(C=O)C>[CH2:3]([O:10][C:11](=[O:27])[NH:12][C:13]1[C:14](=[O:26])[N:15]([CH2:29][C:30](=[O:31])[NH:32][CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])=[CH:17][CH:18]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10089516HCID 10089516, compoundHCID 1428535364297-97-8

Product 1

HCID 57612825HCID 57612825, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of NaH (60% in mineral oil, 287 mg, 7.17 mmol, 1.2 eq.) in anhydrous DMF (12 mL) is added [6-(2-chloro-phenyl)-2-oxo-1,2-dihydro-pyridin-3-yl]-carbamic acid benzyl ester (15A) (Bernstein, P. R. et. al., J. Med. Chem., vol. 37, p 3313-3326 (1994)) (2.121 g, 5.98 mmol). After being stirred for 30 minutes, the orange solution is cooled to 0° C. and 2-iodo-N-phenethyl-acetamide (1.902 g, 6.58 mmol, 1.1 eq.) is added. The mixture is stirred at room temperature for 3 hours and is quenched with 1 N HCl (8 mL), extracted with ethyl acetate (3×). The organic layer is washed in sequence with 1 N HCl, saturated Na2S2O3, water and brine; is dried over anhydrous Na2SO4 and concentrated. The residue is purified via silica gel chromatography (2-10% ethyl acetate in dichloromethane) to provide compound 15B as a yellow solid (605 mg, 20%):

Workup

  1. stirringThe mixture is stirred at room temperature for 3 hours
  2. customis quenched with 1 N HCl (8 mL)
  3. extractionextracted with ethyl acetate (3×)
  4. washThe organic layer is washed in sequence with 1 N HCl, saturated Na2S2O3, water and brine
  5. dry with materialis dried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue is purified via silica gel chromatography (2-10% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-45b930f34e254f3f9336677cf50c16f0
Source dataset
uspto-grants-2011_08
Patent number
US07989441B2

Reaction notes

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