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

HRID 1178002

Reaktionsgleichung

Reaktionsgleichung von HRID 1178002
CCN(C(C)C)C(C)C.[CH2:10]([O:17][C:18]1[CH:32]=[CH:31][C:21]([C:22]([NH:24][C:25]([CH3:30])([CH3:29])[C:26]([OH:28])=O)=[O:23])=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[N:55]1([C:61]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=2[C:69]([F:72])([F:71])[F:70])=[O:62])[CH2:60][CH2:59][NH:58][CH2:57][CH2:56]1>CN(C=O)C.O>[CH2:10]([O:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([NH:24][C:25]([CH3:30])([CH3:29])[C:26](=[O:28])[N:58]2[CH2:59][CH2:60][N:55]([C:61](=[O:62])[C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=3[C:69]([F:72])([F:70])[F:71])[CH2:56][CH2:57]2)=[O:23])=[CH:31][CH:32]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 167337831-(2-Trifluoromethylbenzoyl)piperazine hydrochlorideHCID 578556642-(4-Benzyloxy-benzoylamino)-2-methyl-propionic acid

Produkt 1

HCID 595596074-benzyloxy-N-{1,1-dimethyl-2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamideAusbeute 50,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIPEA (284 mg, 0.19 mL, 1.62 mmol) was added to a stirred solution of 2-(4-benzyloxy-benzoylamino)-2-methyl-propionic acid (170 mg, 0.54 mmol) in DMF (2 mL). HOBT (88 mg, 0.65 mmol) and EDCI (125 mg, 0.65 mmol) were then added at room temperature. After 2 minutes, piperazin-1-yl-(2-trifluoromethyl-phenyl)-methanone hydrochloride salt (192 mg, 0.65 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 150 mg (50% yield) of 4-benzyloxy-N-{1,1-dimethyl-2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide. LCMS Purity: 93.29%. 1H NMR (DMSO-d6): δ 8.4 (bs, 1H), 7.6-7.8 (m, 5H), 7.4 (m, 6H), 7.0-7.1 (d, 2H), 5.2 (m, 2H), 3.5 (m, 5H), 3.0 (m, 3H), 1.4 (s, 6H).

Aufarbeitung

  1. filtrationfiltered the solid
  2. customprecipitated out

Quellen und Nachweise

ORD-Eintrag
ord-70f54ed9e03b4e659104debb51e72d80
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842696B2

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