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

HRID 1177995

Reaktionsgleichung

Reaktionsgleichung von HRID 1177995
CCN(C(C)C)C(C)C.[C:10]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:15]=[CH:14][C:13]([C:16]([N:18]([CH2:20][C:21]([OH:23])=O)[CH3:19])=[O:17])=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[N:52]1([C:58]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=2[C:66]([F:69])([F:68])[F:67])=[O:59])[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]1>CN(C=O)C.O>[CH3:19][N:18]([CH2:20][C:21](=[O:23])[N:55]1[CH2:56][CH2:57][N:52]([C:58](=[O:59])[C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=2[C:66]([F:69])([F:67])[F:68])[CH2:53][CH2:54]1)[C:16]([C:13]1[CH:12]=[CH:11][C:10]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:15][CH:14]=1)=[O:17]

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 167337831-(2-Trifluoromethylbenzoyl)piperazine hydrochlorideHCID 43239699[(Biphenyl-4-carbonyl)-methyl-amino]-acetic acid

Produkt 1

HCID 59559638Biphenyl-4-carboxylic acid methyl-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amideAusbeute 71,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIPEA (216 mg, 0.3 mL, 1.6 mmol) was added to a stirred solution of [(biphenyl-4-carbonyl)-methyl-amino]-acetic acid (100 mg, 0.37 mmol) in DMF (3 mL). HOBT (55.2 mg, 0.4 mmol) and EDCI (178 mg, 0.92 mmol) were then added at room temperature. After 2 minutes piperazin-1-yl-(2-trifluoromethyl-phenyl)-methanone hydrochloride salt (131 mg, 0.44 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and filtered the solid precipitated out to afford 135 mg (71.3% yield) of biphenyl-4-carboxylic acid methyl-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 96.56%. 1H NMR (DMSO-d6): δ 7.9-7.6 (m, 7H), 7.6-7.45 (q, 4H), δ 7.45-7.3 (q, 2H), 4.5-4.2 (m, 2H), 4.15 (s, 1H), 3.8-3.5 (m, 4H), 3.5-3.4 (m, 2H), 3.25-3.1 (m, 2H), 3.0 (s, 3H).

Aufarbeitung

  1. filtrationfiltered the solid
  2. customprecipitated out

Quellen und Nachweise

ORD-Eintrag
ord-2f25f3de09f14ad99655326ba4f5b2ca
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842696B2

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