1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57855650, Verbindung

HRID 1177894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177894
CCN(C(C)C)C(C)C.[C:10]1([C:16]2[S:17][C:18]([C:21]([OH:23])=O)=[CH:19][N:20]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:46][CH2:47][C:48]([N:50]1[CH2:55][CH2:54][N:53]([C:56](=[O:67])[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=2[C:63]([F:66])([F:65])[F:64])[CH2:52][CH2:51]1)=[O:49]>CN(C=O)C.C(OCC)(=O)C.O>[O:49]=[C:48]([N:50]1[CH2:51][CH2:52][N:53]([C:56](=[O:67])[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=2[C:63]([F:66])([F:65])[F:64])[CH2:54][CH2:55]1)[CH2:47][NH:46][C:21]([C:18]1[S:17][C:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:20][CH:19]=1)=[O:23]

Komponenten

9

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1390872-Phenyl-5-carboxythiazoleHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride

Produkt 1

HCID 57855650HCID 57855650, VerbindungAusbeute 35,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

DIPEA (170 mg, 0.22 mL, 1.31 mmol) was added to a stirred solution of 2-phenyl-thiazole-5-carboxylic acid (90 mg, 0.43 mmol) in DMF (2 mL). HOBT (71 mg, 0.52 mmol) and EDCI (100 mg, 0.52 mmol) were then added at room temperature. After 2 minutes 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (185 mg, 0.52 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 77.1 mg (35%) of 2-phenyl-thiazole-5-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 95.1%. 1H NMR (DMSO-d6): δ 9.0-8.9 (m, 1H), 8.54-8.5 (s, 1H), 8.0 (m, 2H), 7.9-7.64 (m, 3H), 7.6-7.5 (m, 4H), 4.24-4.1 (m, 2H), 3.8-3.6 (m, 4H), 3.5-3.4 (m, 2H), 3.2-3.0 (m, 2H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-c22f8b4734f8402ca27391b94efaccc2
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842696B2

Notizen zur Reaktion

Wird geladen…