1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Pentanediamide

HRID 431720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 431720
C(OC1C=CC(CCCl)=C([NH:18][C:19]([C:21]2[O:22][C:23]3C=CC(N)=C[C:24]=3[CH:25]=2)=[O:20])C=1)C1C=CC=CC=1.CC[N:33]=C=NCCCN(C)C.O.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[CH2:25]([CH2:21][C:19]([NH2:18])=[O:20])[CH2:24][C:23]([NH2:33])=[O:22]

Komponenten

5

Edukt 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 187614272-(4-Benzyloxy-2-(5-aminobenzofuran-2-carboxamido)phenyl)ethyl chloride

Produkt 1

HCID 230227PentanediamideAusbeute 395,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To the 2-(4-benzyloxy-2-(5-aminobenzofuran-2-carboxamido)phenyl)ethyl chloride (0.243 mmol) was added the N-[(N-BOC-(4-aminobutyl)-N-methylimidazole-4-(N-methylpyrrole-2-carboxamido)-2-carboxamido)]glutaramide monocarboxylic acid (0.133 g, 0.258 mmol), EDCI (0.093 g, 0.486 mmol) and 1-hydroxybenzotriazole hydrate [HOBT] (0.033 g, 0.244 mmol) which was then dissolved in DMF (15 mL). Dissolution was aided by sonication and the suspension stirred under nitrogen at room temperature for two days with the flask covered with foil. At that time, the DMF was removed via kugelrohr apparatus (0.1 mm Hg, 60° C.). The resulting oil was dissolved in CHCl3, washed with water (1×75 mL), then with brine (1×75 mL) and dried over sodium sulfate. It was then filtered and concentrated under reduced pressure to yield the product N-[(N-BOC-(4-aminobutyl)-N-methylimidazole-4-(N-methylpyrrole-2-carboxamido)-2-carboxamido)]-N-[5-(3-benzyloxy-2-(2-chloroethyl)phenyl)benzofuran-2-carboxamido)]glutarodiamide as a brown oil (0.125 g, 51% yield). Rf=0.40 (10% MeOH/CHCl3) IR (Nujol) 3309, 3190, 1685, 1644, 1536, 1260, 1168, 1096, 1014, 809, 723. 1H-NMR (500 MHz, DMSO-d6) 10.24 (s, 1H), 10.21 (s, 1H), 10.04 (s, 1H), 9.83 (s, 1H), 8.19 (d, 1.5, 1H), 7.90 (t, 6.5, 1H), 7.69 (s, 1H), 7.62 (d, 8.5, 1H), 7.55 (dd, 2.0, 8.5, 1H), 7.46 (s, 1H), 7.44 (d, 8.0, 2H), 7.39 (t, 8.0, 2H), 7.33 (t, 8.0, 1H), 7.30 (d, 8.5, 1H), 7.28 (s, 1H), 7.02 (d, 1.5, 1H), 6.94 (dd, 2.0, 8.5, 1H), 6.90 (d, 1.5, 1H), 6.79 (t br, 1H), 5.09 (s, 2H), 3.91 (s, 3H), 3.82 (s, 3H), 3.76 (t, 6.5, 2H), 3.21 (q, 6.5, 2H), 2.98 (t, 6.5, 2H), 2.90 (t, 6.5, 2H), 2.38 (t, 6.5, 2H), 2.32 (t, 6.5, 2H), 1.91 (quintet, 6.5, 2H), 1.45 (quintet, 6.5, 2H), 1.35 (s, 9H).

Aufarbeitung

  1. dissolutionDissolution
  2. customwas aided by sonication
  3. customAt that time, the DMF was removed via kugelrohr apparatus (0.1 mm Hg, 60° C.)
  4. dissolutionThe resulting oil was dissolved in CHCl3
  5. washwashed with water (1×75 mL)
  6. dry with materialwith brine (1×75 mL) and dried over sodium sulfate
  7. filtrationIt was then filtered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9a269a48242c4552b8cc05f98d8f924a
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660742B2

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