Benzoic Acid → 4-[1,3,4]oxadiazol-2-yl-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide

HRID 1177900Notes

Reaction equation

HRID 1177900 reaction equation
CC[N:3]([CH:7](C)C)C(C)C.[C:10]([OH:18])(=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CCN=C=NCCC[N:27]([CH3:29])C.C1C=CC2N([OH:39])N=NC=2C=1.[NH2:40][CH2:41][C:42]([N:44]1[CH2:49][CH2:48][N:47]([C:50](=[O:61])[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=2[C:57]([F:60])([F:59])[F:58])[CH2:46][CH2:45]1)=[O:43].Cl>CN(C=O)C.O>[O:39]1[CH:7]=[N:3][N:27]=[C:29]1[C:14]1[CH:13]=[CH:12][C:11]([C:10]([NH:40][CH2:41][C:42](=[O:43])[N:44]2[CH2:45][CH2:46][N:47]([C:50](=[O:61])[C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=3[C:57]([F:60])([F:58])[F:59])[CH2:48][CH2:49]2)=[O:18])=[CH:16][CH:15]=1

Participants

9

Reactant 6

HCID 243Benzoic AcidHCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 595596292-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone

Product 1

HCID 251671224-[1,3,4]oxadiazol-2-yl-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamideYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (154 mg, 0.2 mL, 1.19 mmol) was added drop wise to 4-[1,3,4]oxadiazol-2-yl)-benzoic acid (65 mg, 0.34 mmol) in DMF (3 mL). EDCI (98.2 mg, 0.51 mmol) and HOBT (50 mg, 0.37 mmol) were then added. After 2 minutes, 2-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone in its HCl salt form (150 mg, 0.4 mmol) was added. The resulting mixture was stirred at room temperature overnight. Cold water was then added and filtered the solid precipitated to afford 90 mg (54% yield) of 4-[1,3,4]oxadiazol-2-yl-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide. LCMS Purity: 94.4%. 1H NMR (DMSO-d6): δ 9.4 (s, 1H), 8.9 (bs, 1H), 8.5 (s, 1H), 8.15 (dd, 2H), 7.7 (m, 4H), 7.55 (t, 1H), 4.2 (dd, 2H), 3.7 (bs, 4H), 3.5 (s, 1H), 3.1 (d, 3H).

Workup

  1. filtrationfiltered the solid
  2. customprecipitated

Sources & evidence

ORD record
ord-45c774a640864ea5ae8c44c4f08a47b8
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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