Hydrochloric Acid → 1-(1-ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid (1-pyridin-2-yl-butyl)-amide

HRID 1750176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1750176
[CH2:1]([CH:3]([N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]([OH:17])=O)=[CH:14][C:9]=2[N:8]=[C:7]1[CH2:18][C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)[CH2:4][CH3:5])[CH3:2].C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[N:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[CH:49]([NH2:53])[CH2:50][CH2:51][CH3:52].Cl>CN(C=O)C.O.C(Cl)CCl>[N:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[CH:49]([NH:53][C:15]([C:13]1[CH:12]=[CH:11][C:10]2[N:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[C:7]([CH2:18][C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)=[N:8][C:9]=2[CH:14]=1)=[O:17])[CH2:50][CH2:51][CH3:52]

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 227675931-(Pyridin-2-yl)butan-1-amineHCID 867143731-(1-ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid

Produkt 1

HCID 867143891-(1-ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid (1-pyridin-2-yl-butyl)-amideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 50 mg of 1-(1-ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid in 2 ml of dry DMF 10 mg of HOAT, 35 mg of EDC and 0.1 ml of DIPEA were added at 0° C. After 15 min 25 mg of 1-pyridin-2-ylbutylamine were added and the reaction was stirred at rt for 16 h. The reaction was then poured into water and the pH was adjusted to 4 by the addition of 2 M aqueous hydrochloric acid. The reaction was extracted with ethyl acetate three times. The combined organic phases were dried over magnesium sulphate and concentrated. 70 mg (100%) of 1-(1-ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid (1-pyridin-2-yl-butyl)-amide were obtained.

Aufarbeitung

  1. extractionThe reaction was extracted with ethyl acetate three times
  2. dry with materialThe combined organic phases were dried over magnesium sulphate
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-51d50f83f51a486189e2f342e8a54619
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156796B2

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