Piperidine → HCID 68713122, compound

HRID 2069318Notes

Reaction equation

HRID 2069318 reaction equation
[O:1]=[C:2]1[O:6][C:5]([C@H:7]2[CH2:9][C@H:8]2[C:10]([OH:12])=O)=[N:4][N:3]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[NH:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1>CN(C=O)C>[C:13]1([N:3]2[N:4]=[C:5]([C@@H:7]3[CH2:9][C@@H:8]3[C:10]([N:41]3[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]3)=[O:12])[O:6][C:2]2=[O:1])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68713012HCID 68713012, compound

Product 1

HCID 68713122HCID 68713122, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg (0.2 mmol) of cis-2-(5-oxo-4-phenyl-4,5-dihydro-[1,3,4]oxadiazol-2-yl)-cyclopropanecarboxylic acid, 233 mg (2.0 mmol) of NEM and 67 mg (0.2 mmol) of TOTU were dissolved in 2 ml of DMF and stirred at room temperature for 15 min. 17.3 mg (0.2 mmol) of piperidine were added to the reaction solution. After stirring at room temperature for 16 h, the reaction mixture was filtered and the product was purified by preparative RP HPLC eluting with a gradient of 0 to 100% acetonitrile in water (+0.01% TFA). After lyophilization the product was obtained as a white solid. Yield: 44 mg.

Workup

  1. stirringAfter stirring at room temperature for 16 h
  2. filtrationthe reaction mixture was filtered
  3. customthe product was purified by preparative RP HPLC
  4. washeluting with a gradient of 0 to 100% acetonitrile in water (+0.01% TFA)
  5. customAfter lyophilization the product was obtained as a white solid

Sources & evidence

ORD record
ord-3c3d1d7e1fd0465ba54400ce22b596d9
Source dataset
uspto-grants-2012_10
Patent number
US08299102B2

Reaction notes

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