Piperidine → HCID 59152239, compound

HRID 1931403Notes

Reaction equation

HRID 1931403 reaction equation
[O:1]=[C:2]1[O:6][C:5]([CH2:7][CH2:8][C:9]([OH:11])=O)=[N:4][N:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[NH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1>CN(C=O)C>[O:11]=[C:9]([N:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1)[CH2:8][CH2:7][C:5]1[O:6][C:2](=[O:1])[N:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:4]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68536689HCID 68536689, compound

Product 1

HCID 59152239HCID 59152239, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg (0.21 mmol) of 3-(5-oxo-4-phenyl-4,5-dihydro-[1,3,4]oxadiazol-2-yl)-propionic acid, 245 mg (2.13 mmol) of NEM and 77 mg (0.23 mmol) of TOTU were dissolved in 2 ml of DMF and stirred at room temperature for 15 min. 20 mg (0.23 mmol) of piperidine were added, and the reaction mixture was stirred at room temperature for 16 h. After evaporation, the product was purified by silica gel chromatography. Yield: 45 mg.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 16 h
  2. customAfter evaporation
  3. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d604148a44ad456087b724ecefa82405
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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