2-Methoxyethylamine → HCID 49819420, compound

HRID 661272Notes

Reaction equation

HRID 661272 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][O:32][CH2:33][CH2:34][NH2:35]>C(O)C>[CH3:31][O:32][CH2:33][CH2:34][NH:35][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

Participants

4

Reactant 2

HCID 80182-Methoxyethylamine2×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 49819420HCID 49819420, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 100 mg (0.225 mmol) of the oxadiazole from Example 23A in 3.0 ml of ethanol were added 25.6 mg (0.337 mmol) of 2-methoxyethylamine, and then the reaction mixture was stirred at 60 for 3 h. Another 51.2 mg (0.674 mmol) of 2-methoxyethylamine were added, and the mixture was stirred at 60° C. for a further 12 h. This was followed by stirring in the microwave at 80° C. for a further 24 h and then at 120° C. for 45 min. The solvent was removed under reduced pressure and the crude product was purified by means of preparative HPLC. Yield: 15.3 mg (12% of theory)

Workup

  1. stirringthe mixture was stirred at 60° C. for a further 12 h
  2. stirringby stirring in the microwave at 80° C. for a further 24 h
  3. waitat 120° C. for 45 min
  4. customThe solvent was removed under reduced pressure
  5. customthe crude product was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-4c7d05707ca6488a9e1d024fdd2a6b03
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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