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Dicyclohexylcarbodiimide → N-(2-morpholinyl-ethyl)-5-[4,5-bis(4-methoxyphenyl)-1H-imidazol-2-ylthio]-pentanamide

HRID 1708390
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1708390
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([S:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=O)[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.O.ON1C2C=CC=CC=2N=N1.[NH2:41][CH2:42][CH2:43][N:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.C(OCC)(=O)C>[N:44]1([CH2:43][CH2:42][NH:41][C:27](=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23][S:22][C:11]2[NH:10][C:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)=[C:13]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[N:12]=2)[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 4082852-MorpholinoethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 100473085-[4,5-bis(4-methoxyphenyl)-1H-imidazol-2-ylthio]pentanoic acid

Produkt 1

HCID 10052537N-(2-morpholinyl-ethyl)-5-[4,5-bis(4-methoxyphenyl)-1H-imidazol-2-ylthio]-pentanamide

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 5-[4,5-bis(4-methoxyphenyl)-1H-imidazol-2-ylthio]pentanoic acid (1.91 g, 4.63 mmol) and 1-hydroxy-1H-benzotriazole hydrate (890 rag, 6.59 mmol) in tetrahydrofuran (20 mL) was cooled to 0° C., and treated with 2-aminoethylmorpholine (1.0 mL, 7.62 mmol). After 20 minutes, dicyclohexylcarbodiimide (1.42 g, 6.88 mmol) was added in small portions over 20 minutes. This mixture was allowed to stir an additional 48 hours, then poured into ethyl acetate (250 mL), filtered, and washed with water (200 mL). The phases were separated, and the aqueous phase was saturated with sodium chloride and reextracted with methylene chloride (200 mL). The organic phases were combined, dried over anhydrous sodium sulfate and evaporated. The mixture was separated by flash chromatography to afford the product, N-(2-morpholinyl-ethyl)-5-[4,5-bis(4-methoxyphenyl)-1H-imidazol-2-ylthio]-pentanamide, as an oil (1.77 g, 3.37 mmol, 73%). 1H NMR (CDCl3): 7.42 (4H, br d, J=9 Hz); 6.82 (4H, d, J=9 Hz); 6.22 (1H, br t, J=4 Hz); 3.80 (6H, s); 3.65-3.60 (4H, m); 3.15 (2H, q, J=6 Hz); 2.98 (2H, t, J=7 Hz); 2.38-2.24 (8H, m); 1.96-1.85 (2H, m); 1.70-1.60 (2H, m).

Aufarbeitung

  1. filtrationfiltered
  2. washwashed with water (200 mL)
  3. customThe phases were separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe mixture was separated by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d6eaf97ce31548bd875d62dfb38cf9ea
Quelldatensatz
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05358946

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