Water → HCID 66960350, compound

HRID 1362738Notes

Reaction equation

HRID 1362738 reaction equation
[H-].[Na+].[N:3]1([C:9]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][CH2:15][CH:16]3[NH:19][C:20](=[O:41])/[C:21](=[CH:26]/[C:27]3[CH:32]=[CH:31][C:30]([N:33]4[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34]4)=[C:29]([O:39][CH3:40])[CH:28]=3)/[CH2:22][CH2:23][CH2:24]Cl)=[CH:11][CH:10]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.O.C(OCC)(=O)C>CN(C=O)C>[CH3:40][O:39][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][C:30]=1[N:33]1[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34]1)/[CH:26]=[C:21]1/[C:20](=[O:41])[N:19]([CH:16]2[C:17]3[C:12](=[CH:11][CH:10]=[C:9]([N:3]4[CH2:8][CH2:7][O:6][CH2:5][CH2:4]4)[CH:18]=3)[CH2:13][CH2:14][CH2:15]2)[CH2:24][CH2:23][CH2:22]/1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 66961708HCID 66961708, compound

Product 1

HCID 66960350HCID 66960350, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (containing mineral oil at 40%, 37.8 mg) was added to a solution of (E)-5-chloro-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)-benzylidene)valeric acid (7-morpholin-4-yl-1,2,3,4-tetrahydronaphthalen-1-yl)amide (213 mg) in DMF (5.0 mL) at 0° C., and the reaction solution was stirred for 30 minutes. After confirming that the raw materials disappeared, water and ethyl acetate were added to the reaction solution and the organic layer was partitioned. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system) to obtain 195 mg of (E)-3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)-1-(7-morpholin-4-yl-1,2,3,4-tetrahydronaphthalen-1-yl)piperidin-2-one as a racemate.

Workup

  1. customthe organic layer was partitioned
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-222f5ed8160342659b68be5266d6ac2d
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

Loading…