1-Acetylpiperazine → HCID 24946901, compound

HRID 1931389Notes

Reaction equation

HRID 1931389 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:14][C:13]([CH2:15][CH2:16][C:17]([OH:19])=O)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[C:44]([N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1)(=[O:46])[CH3:45]>CN(C=O)C>[C:44]([N:47]1[CH2:52][CH2:51][N:50]([C:17](=[O:19])[CH2:16][CH2:15][C:13]2[S:14][C:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:21])[F:20])=[CH:9][CH:8]=3)=[CH:11][CH:12]=2)[CH2:49][CH2:48]1)(=[O:46])[CH3:45]

Participants

5

Reactant 3

HCID 837951-AcetylpiperazineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68537805HCID 68537805, compound

Product 1

HCID 24946901HCID 24946901, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg (0.16 mmol) of 3-[5-(4-trifluoromethoxy-phenyl) -thiophen-2-yl]-propionic acid, 0.182 g (1.58 mmol) of NEM and 57 mg (0.17 mmol) of TOTU were dissolved in 2 ml of DMF and stirred at room temperature for 15 min. 22 mg (0.17 mmol) of 1-acetyl-piperazine were added, and the reaction mixture was stirred at room temperature for 16 h. After evaporation, 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 solid. Yield: 17 mg.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 16 h
  2. customAfter evaporation
  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 solid

Sources & evidence

ORD record
ord-0d043ed0e83040ebb863b01e376bd992
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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