3-Oxetanamine → Morpholin-4-yl{3-[3-(oxetan-3-ylamino)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethyl)phenyl]-piperidin-1-yl}methanone

HRID 661273Notes

Reaction equation

HRID 661273 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]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH2:10][N:9]([C:23]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:24])[CH2:8]2)[O:4][N:3]=1.[O:31]1[CH2:34][CH:33]([NH2:35])[CH2:32]1>C(O)C>[N:25]1([C:23]([N:9]2[CH2:10][CH:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH2:12][CH:7]([C:5]3[O:4][N:3]=[C:2]([NH:35][CH:33]4[CH2:34][O:31][CH2:32]4)[N:6]=3)[CH2:8]2)=[O:24])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 98339233-OxetanamineHCID 58116540{3-(3-Chloro-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(morpholin-4-yl)methanone

Product 1

HCID 49819421Morpholin-4-yl{3-[3-(oxetan-3-ylamino)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethyl)phenyl]-piperidin-1-yl}methanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 100 mg (0.225 mmol) of the oxadiazole from Example 23A in 1.5 ml of ethanol were added 335 mg (4.50 mmol) of oxetan-3-amine, and then the reaction mixture was stirred at 80 for 3 days. The solvent was removed under reduced pressure and the crude product was purified by means of preparative HPLC. Yield: 59.7 mg (55% 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-c9ac63841fff4df1a1caccb0a117183f
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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