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

HRID 661278Notes

Reaction equation

HRID 661278 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.[CH2:30]([NH:32][CH2:33][CH3:34])[CH3:31]>C(O)C>[CH2:30]([N:32]([CH2:33][CH3:34])[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)[CH3:31]

Participants

4

Reactant 2

HCID 8021Diethylamine2×HCID 58116548[3-(3-Chloro-1,2,4-oxadiazol-5-yl)-5-(4-ethylphenyl)piperidin-1-yl](4-hydroxypiperidin-1-yl)-methanone

Product 1

HCID 49819561{3-[3-(Diethylamino)-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 45.0 mg (0.098 mmol) of the oxadiazole from Example 25A in 0.61 ml of ethanol were added 143 mg (1.96 mmol) of diethylamine, and then the reaction mixture was stirred in the microwave at 80 for 5 h. Another 143 mg (1.96 mmol) of diethylamine were added and the mixture was stirred in the microwave at 80° C. for a further 2 h. The solvent was removed under reduced pressure and the crude product was purified by means of preparative HPLC. Yield: 35.6 mg (80% of theory)

Workup

  1. stirringthe mixture was stirred in the microwave at 80° C. for a further 2 h
  2. customThe solvent was removed under reduced pressure
  3. customthe crude product was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-355168af44f2444db260efe596545500
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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