1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-(3-Trifluoromethyl-phenyl)-furan-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide

HRID 1177948Notes

Reaction equation

HRID 1177948 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.[F:60][C:61]([F:77])([F:76])[C:62]1[CH:63]=[C:64]([C:68]2[O:72][C:71]([C:73](O)=[O:74])=[CH:70][CH:69]=2)[CH:65]=[CH:66][CH:67]=1>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:73]([C:71]1[O:72][C:68]([C:64]2[CH:65]=[CH:66][CH:67]=[C:62]([C:61]([F:77])([F:60])[F:76])[CH:63]=2)=[CH:69][CH:70]=1)=[O:74]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6882815-(3-(Trifluoromethyl)phenyl)-2-furoic acidHCID 866340882-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt

Product 1

HCID 251673275-(3-Trifluoromethyl-phenyl)-furan-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amideYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (75 mg, 0.1 mL, 0.59 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt (100 mg, 0.23 mmol) in DMF (1 mL). HOBT (32 mg, 0.23 mmol) and EDCI (44 mg, 0.23 mmol) were then added at room temperature. After 2 minutes, 5-(3-trifluoromethyl-phenyl)-furan-2-carboxylic acid (50 mg, 0.20 mmol) was added and the resulting mixture was stirred at room temperature for 4 hrs. Cold water 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 40 mg (37% yield) of 5-(3-trifluoromethyl-phenyl)-furan-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 86.88%. 1H NMR (DMSO-d6): δ 8.8-8.7 (t, 1H), 8.3 (s, 1H), 8.2 (t, 1H), 7.9-7.6 (m, 5H), 7.6-7.5 (t, 1H), 7.4-7.3 (d, 1H), 7.3-7.2 (m, 1H), 4.3-4.1 (m, 2H), 3.8-3.4 (m, 6H), 3.2-3.1 (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-5b82bbb7ee724d83aac5ebf6addb86d3
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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