5-Nitro-2-Furoic Acid → 5-Nitro-furan-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide

HRID 1178058Notes

Reaction equation

HRID 1178058 reaction equation
CCN(C(C)C)C(C)C.OC(C(F)(F)F)=O.[NH2:17][CH2:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([C:27](=[O:38])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]([F:37])([F:36])[F:35])[CH2:23][CH2:22]1)=[O:20].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[N+:61]([C:64]1[O:68][C:67]([C:69](O)=[O:70])=[CH:66][CH:65]=1)([O-:63])=[O:62]>CN(C=O)C.O>[O:20]=[C:19]([N:21]1[CH2:22][CH2:23][N:24]([C:27](=[O:38])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]([F:37])([F:35])[F:36])[CH2:25][CH2:26]1)[CH2:18][NH:17][C:69]([C:67]1[O:68][C:64]([N+:61]([O-:63])=[O:62])=[CH:65][CH:66]=1)=[O:70]

Participants

8

Reactant 5

HCID 125775-Nitro-2-Furoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866340882-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt

Product 1

HCID 251647215-Nitro-furan-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amideYield 49.12%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (50 mg, 0.38 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone-TFA salt (66 mg, 0.15 mmol) in DMF (1 mL). HOBT (21 mg, 0.15 mmol) and EDCI.HCl (29 mg, 0.15 mmol) were added at room temperature. After 2 minutes, 5-nitro-furan-2-carboxylic acid (20 mg, 0.13 mmol) was added. The resulting mixture was stirred at room temperature for four hours. Water was then added, and the product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Purification by column chromatography (using silica gel of mesh size of 60-120 and 3% methanol in chloroform as the eluent) afforded 28 mg (49.12% yield) of 5-nitro-furan-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 97.329%, HPLC Purity %: 95.234, 1H NMR (CDCl3): δ 7.8-7.7 (d, 1H), 7.7-7.5 (m, 3H), 7.4-7.3 (m, 2H), 4.4-4.3 (t, 1H), 4.2 (bt, 1H), 4.1-3.8 (m, 2H), 3.8-3.5 (m, 4H), 3.4 (bt, 1H), 3.3-3.2 (m, 2H).

Workup

  1. extractionthe product was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by column chromatography (

Sources & evidence

ORD record
ord-03d5342ee923427d941e20fd449b22d1
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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