1-Hydroxybenzotriazole → Thiophene-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazine-1-yl]-ethyl}-amide

HRID 1178075

Reaktionsgleichung

Reaktionsgleichung von HRID 1178075
CCN(C(C)C)C(C)C.[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]([NH:17][CH2:18][C:19]([OH:21])=O)=[O:16].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[N:45]1([C:51]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[C:59]([F:62])([F:61])[F:60])=[O:52])[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1>CN(C=O)C.O>[O:21]=[C:19]([N:48]1[CH2:49][CH2:50][N:45]([C:51](=[O:52])[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[C:59]([F:62])([F:60])[F:61])[CH2:46][CH2:47]1)[CH2:18][NH:17][C:15]([C:11]1[S:10][CH:14]=[CH:13][CH:12]=1)=[O:16]

Komponenten

8

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 679227((2-Thienylcarbonyl)amino)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 167337831-(2-Trifluoromethylbenzoyl)piperazine hydrochloride

Produkt 1

HCID 59559594Thiophene-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazine-1-yl]-ethyl}-amideAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIPEA (0.130 mL, 0.76 mmol) was added to a stirred solution of [(thiophene-2-carbonyl)-amino]-acetic acid (40 mg, 0.22 mmol) in DMF (1 mL). HOBT (35 mg, 0.26 mmol) and EDCI.HCl (49 mg, 0.26 mmol) were added, followed by the addition of piperazine-1-yl-(2-trifluoromethyl-phenyl)-methanone hydrochloride (70 mg, 0.24 mmol) at room temperature. The reaction mixture was stirred at room temperature overnight. Water was then added, and the product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford thiophene-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazine-1-yl]-ethyl}-amide in 54% yield. LC-MS purity: 98% 1H NMR (CDCL3): δ 7.78-7.44 (m, 5H), 7.34 (t, 1H), 7.10 (d, 2H), 4.40-4.18 (m, 2H), 4.08-3.82 (m, 2H), 3.80-3.50 (m, 4H).

Aufarbeitung

  1. extractionthe product was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7e0cdb954bdd4ccc89017403f6c1cbd6
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842696B2

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