2-Thiopheneacetic acid → 4-(2-Ethyl-cyclohexylamino)-3-(2-thiophen-2-yl-acetylamino)-benzoic acid methyl ester

HRID 1750250Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1750250
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([OH:9])=O.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:29][O:30][C:31](=[O:48])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][CH:39]2[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]2[CH2:45][CH3:46])=[C:34]([NH2:47])[CH:33]=1>CN(C=O)C.O.C(Cl)CCl>[CH3:29][O:30][C:31](=[O:48])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][CH:39]2[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]2[CH2:45][CH3:46])=[C:34]([NH:47][C:7](=[O:9])[CH2:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[CH:33]=1

Komponenten

8

Edukt 4

HCID 159702-Thiopheneacetic acidHCID 81531Diisopropylethylamine2×HCID 181649HOAtHCID 614680353-Amino-4-(2-ethyl-cyclohexylamino)-benzoic acid methyl ester

Produkt 1

HCID 867144564-(2-Ethyl-cyclohexylamino)-3-(2-thiophen-2-yl-acetylamino)-benzoic acid methyl esterAusbeute 101 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 0.24 g of thiophen-2-yl-acetic acid in 40 ml of dry DMF 0.11 g of HOAT, 0.36 g of EDC and 0.5 ml of DIPEA were added at 0° C. After 30 min 0.41 g of 3-Amino-4-(2-ethyl-cyclohexylamino)-benzoic acid methyl ester were added, followed by the addition of 0.5 ml of DIPEA and the reaction was stirred at rt for 48 h. The reaction was then poured into water and extracted with ethyl acetate three times. The combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulphate and concentrated to obtain 0.60 g (97%) of 4-(2-Ethyl-cyclohexylamino)-3-(2-thiophen-2-yl-acetylamino)-benzoic acid methyl ester, which was used without further purification.

Aufarbeitung

  1. extractionextracted with ethyl acetate three times
  2. washThe combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7e9aff7c81b24f5e95761f7d59b77151
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156796B2

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