Cyclopropylamine → {3-[3-(Cyclopropylamino)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}-(morpholin-4-yl)methanone

HRID 661270Notes

Reaction equation

HRID 661270 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.[CH:31]1([NH2:34])[CH2:33][CH2:32]1>C(O)C>[CH:31]1([NH:34][C:2]2[N:6]=[C:5]([CH:7]3[CH2:12][CH:11]([C:13]4[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=4)[CH2:10][N:9]([C:23]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[O:24])[CH2:8]3)[O:4][N:3]=2)[CH2:33][CH2:32]1

Participants

4

Reactant 2

HCID 69828Cyclopropylamine2×HCID 58116540{3-(3-Chloro-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(morpholin-4-yl)methanone

Product 1

HCID 49819289{3-[3-(Cyclopropylamino)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}-(morpholin-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 150 mg (0.337 mmol) of the oxadiazole from Example 23A in 1.5 ml of ethanol were added 385 mg (6.74 mmol) of cyclopropylamine, and then the reaction mixture was stirred in the microwave at 80 for 2 h. Another 385 mg (6.74 mmol) of cyclopropylamine were added and the mixture was stirred in the microwave at 80° C. for a further 2 h. This was followed by stirring in the microwave at 90° C. for 1 h. The solvent was removed under reduced pressure and the crude product was purified by means of preparative HPLC. Yield: 95.3 mg (61% of theory)

Workup

  1. stirringthe mixture was stirred in the microwave at 80° C. for a further 2 h
  2. stirringby stirring in the microwave at 90° C. for 1 h
  3. customThe solvent was removed under reduced pressure
  4. customthe crude product was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-3f64de908d83457b8c86b2505b6a5899
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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