Azetidine → {3-[3-(Azetidin-1-yl)-1,2,4-oxadiazol-5-yl]-5-(4-ethylphenyl)piperidin-1-yl}(4-hydroxypiperidin-1-yl)methanone

HRID 661280Notes

Reaction equation

HRID 661280 reaction equation
Cl[C:2]1[N:6]=[C:5]([CH:7]2[CH2:12][CH:11]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=3)[CH2:10][N:9]([C:21]([N:23]3[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25][CH2:24]3)=[O:22])[CH2:8]2)[O:4][N:3]=1.[NH:30]1[CH2:33][CH2:32][CH2:31]1>C(O)C>[N:30]1([C:2]2[N:6]=[C:5]([CH:7]3[CH2:12][CH:11]([C:13]4[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=4)[CH2:10][N:9]([C:21]([N:23]4[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25][CH2:24]4)=[O:22])[CH2:8]3)[O:4][N:3]=2)[CH2:33][CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 58116548[3-(3-Chloro-1,2,4-oxadiazol-5-yl)-5-(4-ethylphenyl)piperidin-1-yl](4-hydroxypiperidin-1-yl)-methanone

Product 1

HCID 49819562{3-[3-(Azetidin-1-yl)-1,2,4-oxadiazol-5-yl]-5-(4-ethylphenyl)piperidin-1-yl}(4-hydroxypiperidin-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 80.0 mg (0.174 mmol) of the oxadiazole from Example 25A in 1.10 ml of ethanol were added 198 mg (3.48 mmol) of azetidine, and then the reaction mixture was stirred in the microwave at 80 for 2 h. The solvent was removed under reduced pressure and the crude product was purified by means of preparative HPLC. Yield: 46.9 mg (61% of theory)

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-c37935ac9b424aba94d2c48296c3b609
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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