4-Cyanobenzoic acid → HCID 25164323, compound

HRID 1177954Notes

Reaction equation

HRID 1177954 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.[C:61]([C:63]1[CH:71]=[CH:70][C:66]([C:67](O)=[O:68])=[CH:65][CH:64]=1)#[N:62]>CN(C=O)C.O>[C:61]([C:63]1[CH:71]=[CH:70][C:66]([C:67]([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:68])=[CH:65][CH:64]=1)#[N:62]

Participants

8

Reactant 5

HCID 120874-Cyanobenzoic 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 25164323HCID 25164323, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (53 mg, 0.41 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt (69 mg, 0.16 mmol) in DMF (1 mL). HOBT (22 mg, 0.16 mmol) and EDCI.HCl (31 mg, 0.16 mmol) were then added at room temperature. After 2 minutes, 4-cyanobenzoic acid (20 mg, 0.14 mmol) was added and the resulting mixture was stirred at room temperature for 4 hrs. Cold water (20 mL) was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford 30 mg (50% yield) of 4-cyano-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide. LCMS Purity: 96.9%, 1H NMR (CDCl3): δ 7.9 (d, 2H), 7.8-7.7 (d, 3H), 7.6 (m, 2H), 7.4-7.3 (d, 2H), 4.2 (m, 2H), 4.4-4.2 (m, 2H), 4.0 (m, 2H), 3.8-3.4 (m, 5H), 3.4 (t, 1H), 3.2 (m, 2H).

Workup

  1. extractionthe product was extracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f5e3023ad75b4e78b678f75be19a2ed3
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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