3-(Chloromethyl)-5-phenyl-1,2,4-oxadiazole → HCID 54766236, compound

HRID 1044069

Reaction equation

HRID 1044069 reaction equation
[Cl:1][CH2:2][C:3]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][N:4]=1.[C:14]1([CH:20]([NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:39])[C:21]([O:23][C@@H:24]2[CH:29]3[CH2:30][CH2:31][N:26]([CH2:27][CH2:28]3)[CH2:25]2)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C.C(OCC)(=O)C>[Cl-:1].[C:8]1([C:6]2[O:5][N:4]=[C:3]([CH2:2][N+:26]34[CH2:27][CH2:28][CH:29]([CH2:30][CH2:31]3)[C@@H:24]([O:23][C:21](=[O:22])[CH:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[CH3:39])[CH2:25]4)[N:7]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 3021543-(Chloromethyl)-5-phenyl-1,2,4-oxadiazoleHCID 46840573(R)-quinuclidin-3-yl 2-phenyl-2-(o-tolylamino)acetate

Product 1

HCID 54766236HCID 54766236, compoundYield 19.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(Chloromethyl)-5-phenyl-1,2,4-oxadiazole (I45) (79 mg, 0.40 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-phenyl-2-(o-tolylamino)acetate (I23) (129 mg, 0.37 mmol) in acetonitrile (1.2 ml) and ethyl acetate (2.4 ml). The yellow solution was stirred at room temperature for 48 hours. The solution was evaporated, and the residue was purified by flash chromatography (DCM/MeOH=9/1) to obtain (3R)-1-((5-phenyl-1,2,4-oxadiazol-3-yl)methyl)-3-(2-phenyl-2-(o-tolylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane chloride (39 mg, 19% yield, mixture of diastereomers).

Workup

  1. customThe solution was evaporated
  2. customthe residue was purified by flash chromatography (DCM/MeOH=9/1)

Sources & evidence

ORD record
ord-e0eddd1fcbfc4ded98c93537f94d1c73
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Linked notes

Loading…