Potassium Carbonate → HCID 70869460, compound

HRID 1777365Notes

Reaction equation

HRID 1777365 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10]([C:12]1([CH2:18][O:19][CH3:20])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:11])[CH3:8].[Cl:21][C:22]1[CH:23]=[C:24]([C:33]2[O:37][N:36]=[C:35]([C:38]3[CH:43]=[CH:42][C:41]([CH2:44]Cl)=[CH:40][CH:39]=3)[N:34]=2)[CH:25]=[CH:26][C:27]=1[CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1>CN(C)C=O>[CH2:7]([O:9][C:10]([C:12]1([CH2:18][O:19][CH3:20])[CH2:13][CH2:14][N:15]([CH2:44][C:41]2[CH:40]=[CH:39][C:38]([C:35]3[N:34]=[C:33]([C:24]4[CH:25]=[CH:26][C:27]([CH:28]5[CH2:32][CH2:31][CH2:30][CH2:29]5)=[C:22]([Cl:21])[CH:23]=4)[O:37][N:36]=3)=[CH:43][CH:42]=2)[CH2:16][CH2:17]1)=[O:11])[CH3:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70869465HCID 70869465, compoundHCID 86715144HCID 86715144, compound

Product 1

HCID 70869460HCID 70869460, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
67.5 °C

Procedure

Potassium carbonate (0.28 g, 0.002 mol) and 4-methoxymethylpiperidine-4-carboxylic acid ethyl ester (0.4 g, 0.002 mol) are added to a solution of 5-(3-Chloro-4-cyclopentylphenyl)-3-(4-chloromethyl-phenyl)-[1,2,4]oxadiazole (0.5 g, 0.0013 mol) in N,N-dimethylformamide (15 mL). The reaction mixture is heated at 65-70° C. for 2 hours. Removal of solvent gives a crude residue which is purified by column chromatography (silica gel 230-400 mesh, toluene:ethyl acetate 4:1) to give 1-{4-[5-(3-chloro-4-cyclopentylphenyl)-[1,2,4]-oxadiazol-3-yl]benzyl}-4-methoxy methyl piperidine-4-carboxylic acid ethyl ester.

Workup

  1. customRemoval of solvent
  2. customgives a crude residue which
  3. customis purified by column chromatography (silica gel 230-400 mesh, toluene:ethyl acetate 4:1)

Sources & evidence

ORD record
ord-e83f5d992afc49188bf65f5636c34f96
Source dataset
uspto-grants-2016_02
Patent number
US09266867B2

Reaction notes

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