HCID 58556944, compound → HCID 54766851, compound

HRID 1044072Notes

Reaction equation

HRID 1044072 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][CH:9]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:10]([O:12][C@@H:13]2[CH:18]3[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]3)[CH2:14]2)=[O:11])[CH:5]=[CH:6][CH:7]=1.[Cl:27][CH2:28][C:29]1[N:33]=[C:32]([C:34]2[S:35][CH:36]=[CH:37][N:38]=2)[O:31][N:30]=1>CCOC(C)=O>[Cl-:27].[F:1][C:2]1[CH:3]=[C:4]([NH:8][CH:9]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:10]([O:12][C@@H:13]2[CH:18]3[CH2:19][CH2:20][N+:15]([CH2:28][C:29]4[N:33]=[C:32]([C:34]5[S:35][CH:36]=[CH:37][N:38]=5)[O:31][N:30]=4)([CH2:16][CH2:17]3)[CH2:14]2)=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 58556944HCID 58556944, compoundHCID 58556945HCID 58556945, compound

Product 1

HCID 54766851HCID 54766851, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-quinuclidin-3-yl 2-(3-fluorophenylamino)-2-phenylacetate (I41) (76 mg, 0.21 mmol) in EtOAc (5 mL), was added 3-(chloromethyl)-5-(thiazol-2-yl)-1,2,4-oxadiazole (I55) (43 mg, 0.21 mmol). The mixture was stirred at room temperature for 17 hours. Then the mixture was heated under microwave irradiation at 100° C. for 1 hour. The solvent was evaporated and the crude was triturated with Et2O and filtrated to collect (3R)-3-(2-(3-fluorophenylamino)-2-phenylacetoxy)-1-((5-(thiazol-2-yl)-1,2,4-oxadiazol-3-yl)methyl)-1-azoniabicyclo[2.2.2]octane chloride (36 mg, 30.4% yield, mixture of diastereomers).

Workup

  1. temperatureThen the mixture was heated under microwave irradiation at 100° C. for 1 hour
  2. customThe solvent was evaporated
  3. customthe crude was triturated with Et2O
  4. filtrationfiltrated

Sources & evidence

ORD record
ord-56f178009a5a4ede86d69f80125c6b66
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Reaction notes

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