1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-4-pyridin-2-yl-benzamide

HRID 1177888Notes

Reaction equation

HRID 1177888 reaction equation
CCN(C(C)C)C(C)C.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:47][CH2:48][C:49]([N:51]1[CH2:56][CH2:55][N:54]([C:57](=[O:68])[C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=2[C:64]([F:67])([F:66])[F:65])[CH2:53][CH2:52]1)=[O:50]>CN(C=O)C.C(OCC)(=O)C.O>[O:50]=[C:49]([N:51]1[CH2:52][CH2:53][N:54]([C:57](=[O:68])[C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=2[C:64]([F:67])([F:66])[F:65])[CH2:55][CH2:56]1)[CH2:48][NH:47][C:20](=[O:22])[C:19]1[CH:18]=[CH:17][C:16]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][N:10]=2)=[CH:24][CH:23]=1

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 8216924-(2-Pyridyl)Benzoic AcidHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride

Product 1

HCID 57855667N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-4-pyridin-2-yl-benzamideYield 19.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

DIPEA (116.32 mg, 0.15 mL, 0.9 mmol) was added to a stirred solution of 4-pyridin-2-yl-benzoic acid (60 mg, 0.3 mmol) in DMF (1.5 mL). HOBT (48 mg, 0.36 mmol) and EDCI (70 mg, 0.36 mmol) were then added at room temperature. After 2 minutes 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (127 mg, 0.36 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and then extrated with ethyl acetate. The organic layer was washed with brine and dried over Na2SO4 and concentrated under reduced pressure to afford 29 mg (19.46%) of N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-4-pyridin-2-yl-benzamide. LCMS Purity: 89.36%. 1H NMR (DMSO-d6): δ 9-8.9 (d, 1H), 8.6 (d, 1H), 8.5 (m, 1H), 8.2-8.1 (dt, 1H), 8.0 (d, 2H), 7.9-7.6 (m, 5H), 7.6-7.5 (m, 2H), 4.2 (m, 2H), 3.8-3.6 (m, 4H), 3.2-3.4 (m, 2H), 3.2-3 (m, 2H).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d359ba07ba2a41f8bfa6b5f17eae7216
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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