4-Nitrobenzoic Acid → HCID 25164321, compound

HRID 1178057Notes

Reaction equation

HRID 1178057 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[CH:72]=[CH:71][C:67]([C:68](O)=[O:69])=[CH:66][CH:65]=1)([O-:63])=[O:62]>CN(C=O)C.O>[N+:61]([C:64]1[CH:65]=[CH:66][C:67]([C:68]([NH:17][CH2:18][C:19](=[O:20])[N:21]2[CH2:22][CH2:23][N:24]([C:27](=[O:38])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([F:37])([F:35])[F:36])[CH2:25][CH2:26]2)=[O:69])=[CH:71][CH:72]=1)([O-:63])=[O:62]

Participants

8

Reactant 5

HCID 61084-Nitrobenzoic 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 25164321HCID 25164321, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (47 mg, 0.36 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone-TFA salt (62 mg, 0.14 mmol) in DMF (0.5 mL). HOBT (19 mg, 0.14 mmol) and EDCI.HCl (28 mg, 0.14 mmol) were added at room temperature. After 2 minutes, 4-nitro benzoic acid (20 mg, 0.12 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 to afford 40.7 mg (74% yield) of 4-Nitro-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide. LCMS Purity: 88.67%, HPLC Purity: 92.93%, 1H NMR (CDCl3): δ 8.3 (d, 2H), 8.0 (m, 2H), 7.8-7.7 (d, 1H), 7.6 (m, 2H), 7.4-7.3 (d, 2H), 4.4-4.3 (dd, 1H), 4.3-4.2 (dd, 2H), 4.1-3.9 (m, H), 3.8-3.7 (m, 2H), 3.6 (m, 2H), 3.4 (bt, 1H), 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

Sources & evidence

ORD record
ord-e1ded9396c6b422a9adaac3f9cc57621
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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