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

HRID 661271Notes

Reaction equation

HRID 661271 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.[CH3:31][C:32]1([NH2:36])[CH2:35][CH2:34][CH2:33]1>C(O)C>[CH3:31][C:32]1([NH:36][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)[CH2:35][CH2:34][CH2:33]1

Participants

4

Reactant 2

HCID 14988399(1-Methylcyclobutyl)amine3×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 49819290(3-{3-[(1-Methylcyclobutyl)amino]-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 100 mg (0.225 mmol) of the oxadiazole from Example 23A in 1.5 ml of ethanol were added 383 mg (4.50 mmol) of 1-methylcyclobutanamine, and then the reaction mixture was stirred in the microwave at 80 for 2 h and then at 90° C. for 2 h. Another 383 mg (4.50 mmol) of 1-methylcyclobutanamine were added and the mixture was stirred in the microwave at 90° C. for a further 6 h and then at 100° C. for 6 h. Subsequently, another 383 mg (4.50 mmol) of 1-methylcyclobutanamine were added and the mixture was stirred in the microwave at 100 for a further 20 h. The solvent was removed under reduced pressure and the crude product was purified by means of preparative HPLC. Yield: 27.2 mg (24% of theory)

Workup

  1. waitat 90° C. for 2 h
  2. stirringthe mixture was stirred in the microwave at 90° C. for a further 6 h
  3. waitat 100° C. for 6 h
  4. stirringthe mixture was stirred in the microwave at 100 for a further 20 h
  5. customThe solvent was removed under reduced pressure
  6. customthe crude product was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-b145a77dd1bd4bb0844b03be965394d7
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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