1,2-Dichloroethane → HCID 58754890, Verbindung

HRID 1619210Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619210
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.BrC1SC=CN=1.[Cl:18][C:19]1[CH:20]=[C:21]([C:25]2[CH:30]=[CH:29][C:28]([C:31](O)=[O:32])=[CH:27][CH:26]=2)[CH:22]=[CH:23][CH:24]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.O.CCOC(C)=O>[Cl:18][C:19]1[CH:20]=[C:21]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([N:9]3[CH2:8][CH2:7][N:6]([C:2]4[S:1][CH:5]=[CH:4][N:3]=4)[CH2:11][CH2:10]3)=[O:32])=[CH:27][CH:26]=2)[CH:22]=[CH:23][CH:24]=1

Komponenten

9

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 764302-BromothiazoleHCID 9118061-(Thiazol-2-yl)piperazineHCID 27574173'-Chloro[1,1'-biphenyl]-4-carboxylic acid

Produkt 1

HCID 58754890HCID 58754890, VerbindungAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1-(thiazol-2-yl)piperazine (ca. 0.915 mmol, prepared from 150 mg 2-bromothiazole according to the methods described in Astles et al., J. Med. Chem., 39: 1423-1432 (1996)), 3′-chloro-biphenyl-4-carboxylic acid (212.9 mg, 0.915 mmol) in CH2Cl2 (4 ml), was added EDC (209.7 mg, 1.098 mmol) and HOBt (148.2 mg, 1.098 mmol). After being stirred overnight, the mixture was treated with EtOAc (50 ml) and water (15 ml). The organic phase was washed with brine (5 ml), dried (MgSO4), filtered, and concentrated under reduced pressure to furnish the crude product. This material was purified by column chromatography (20% acetone/hexanes) to give the title compound (225 mg, 64% for two steps) as a white solid: 1H NMR (CDCl3, 400 MHz) δ 7.64-7.23 (m, 9H), 6.65 (t, J=3.6 Hz, 1H), 4.92 (m, br, 2H), 3.57 (m, br, 6H), 3.68 (m, 2H), 2.14 (m, 2H), 1.83 (m, 2H); MS calc'd for C20H19ClN3OS [M+H]+: 384; Found: 384.

Aufarbeitung

  1. washThe organic phase was washed with brine (5 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto furnish the crude product
  6. customThis material was purified by column chromatography (20% acetone/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-edd1667b70a44c6496ea02cab0e4021a
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772291B2

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