3-(Chloromethyl)-5-phenyl-1,2,4-oxadiazole → HCID 86660295, compound

HRID 1044068Notes

Reaction equation

HRID 1044068 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.[CH3:14][NH:15][C:16]([C:18]1[CH:19]=[C:20]([NH:24][CH:25]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:26]([O:28][C@@H:29]2[CH:34]3[CH2:35][CH2:36][N:31]([CH2:32][CH2:33]3)[CH2:30]2)=[O:27])[CH:21]=[CH:22][CH:23]=1)=[O:17]>C(OCC)(=O)C.C(#N)C>[Cl-:1].[CH3:14][NH:15][C:16]([C:18]1[CH:19]=[C:20]([NH:24][CH:25]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:26]([O:28][C@@H:29]2[CH:34]3[CH2:35][CH2:36][N+:31]([CH2:2][C:3]4[N:7]=[C:6]([C:8]5[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=5)[O:5][N:4]=4)([CH2:32][CH2:33]3)[CH2:30]2)=[O:27])[CH:21]=[CH:22][CH:23]=1)=[O:17]

Participants

5

Reactant 2

HCID 3021543-(Chloromethyl)-5-phenyl-1,2,4-oxadiazoleHCID 58556929HCID 58556929, compound

Product 1

HCID 86660295HCID 86660295, compoundYield 15.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(Chloromethyl)-5-phenyl-1,2,4-oxadiazole (I45) (53.9 mg, 0.28 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(3-(methylcarbamoyl)-phenylamino)-2-phenylacetate (I10) (99 mg, 0.252 mmol) in a mixture of ethyl acetate (3.3 ml) and acetonitrile (1.7 ml). The reaction was stirred at room temperature for 2 days. Then the solution was evaporated and the residue was triturated with EtOAc (10 ml). The suspension was filtered on a buckner funnel, and the solid was recovered and further purified by flash chromatography (DCM/MeOH=85/15) to obtain (R)-3-(2-(3-(methylcarbamoyl)phenylamino)-2-phenylacetoxy)-1-((5-phenyl-1,2,4-oxadiazol-3-yl)methyl)-1-azoniabicyclo[2.2.2]octane chloride (23 mg, 15% yield, mixture of diastereomers).

Workup

  1. customThen the solution was evaporated
  2. customthe residue was triturated with EtOAc (10 ml)
  3. filtrationThe suspension was filtered on a buckner funnel
  4. customthe solid was recovered
  5. customfurther purified by flash chromatography (DCM/MeOH=85/15)

Sources & evidence

ORD record
ord-8df78ebe12604995b2e091f06c6a8462
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Reaction notes

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