3-(Chloromethyl)-5-phenyl-1,2,4-oxadiazole → HCID 86688881, compound

HRID 404620Notes

Reaction equation

HRID 404620 reaction equation
[C:1]1([CH:7]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:8]([O:10][C@@H:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:25][CH2:26][C:27]1[N:31]=[C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:29][N:28]=1>CCOC(C)=O.C(#N)C>[Cl-:25].[C:32]1([C:30]2[O:29][N:28]=[C:27]([CH2:26][N+:13]34[CH2:18][CH2:17][CH:16]([CH2:15][CH2:14]3)[C@@H:11]([O:10][C:8](=[O:9])[CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:12]4)[N:31]=2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 2

HCID 3021543-(Chloromethyl)-5-phenyl-1,2,4-oxadiazoleHCID 71603247(R)-quinuclidin-3-yl 2-phenyl-2-(piperidin-1-yl)acetate

Product 1

HCID 86688881HCID 86688881, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-quinuclidin-3-yl 2-phenyl-2-(piperidin-1-yl)acetate (100 mg, 0.30 mmol) in EtOAc (2 ml) and acetonitrile (1 ml), was added 3-(chloromethyl)-5-phenyl-1,2,4-oxadiazole (71.1 mg, 0.36 mmol). The reaction was stirred at room temperature for 30 hours and then the solvents were evaporated. The residue was triturated with EtOAc (10 ml) and the solid was collected by suction filtration to obtain the title compound (113 mg, 71% yield) as a yellow solid.

Workup

  1. customthe solvents were evaporated
  2. customThe residue was triturated with EtOAc (10 ml)
  3. filtrationthe solid was collected by suction filtration

Sources & evidence

ORD record
ord-cda9a5a040b84f9587363928bc0e3cde
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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