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

HRID 1177881Notes

Reaction equation

HRID 1177881 reaction equation
CCN(C(C)C)C(C)C.[CH:10]1[C:18]2[C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[O:15][C:14]=2[CH:13]=[CH:12][C:11]=1[C:23]([OH:25])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.FC(F)(F)C(O)=O.[NH2:54][CH2:55][C:56]([N:58]1[CH2:63][CH2:62][N:61]([C:64](=[O:75])[C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][C:66]=2[C:71]([F:74])([F:73])[F:72])[CH2:60][CH2:59]1)=[O:57]>CN(C=O)C.O>[O:57]=[C:56]([N:58]1[CH2:59][CH2:60][N:61]([C:64](=[O:75])[C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][C:66]=2[C:71]([F:74])([F:73])[F:72])[CH2:62][CH2:63]1)[CH2:55][NH:54][C:23]([C:11]1[CH:12]=[CH:13][C:14]2[O:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[C:18]=2[CH:10]=1)=[O:25]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 4174048-Oxatricyclo(7.4.0.0,2,7)trideca-1(9),2(7),3,5,10,12-hexaene-4-carboxylic acidHCID 866340882-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt

Product 1

HCID 59559637Dibenzofuran-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amideYield 33.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (137 mg, 0.18 mL, 1.06 mmol) was added to a stirred solution of dibenzofuran-2-carboxylic acid (75 mg, 0.35 mmol) in DMF (3 mL). HOBT (47.8 mg, 0.35 mmol) and EDCI (81.3 mg, 0.42 mmol) were then added at room temperature. After 2 minutes 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone trifluoroacetic acid salt (166 mg, 0.38 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added, filtered the solid precipitated to afford 60 mg (33.3%) of dibenzofuran-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 97.09%. 1H NMR (DMSO-d6): δ 8.7 (bs, 2H), 8.2 (d, 1H), 8.06 (d, 1H), 7.9-7.55 (m, 7H), 7.55 (t, 1H), 4.41-4.3 (bs, 2H), 3.8-3.6 (bs, 4H), 3.5-3.4 (bs, 2H), 3.2-3.0 (bs, 2H).

Workup

  1. filtrationfiltered the solid
  2. customprecipitated

Sources & evidence

ORD record
ord-da3c82b78e184cd6859a7284c71df3ff
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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