Triethylamine → Ethyl 3-{5-[(2-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

HRID 1676051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1676051
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]([CH:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[N:8][C:4]=2[CH:3]=1.C(N(CC)CC)C.[N+:31]([C:34]1[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=1[C:36](Cl)=[O:37])([O-:33])=[O:32]>ClCCl>[N+:31]([C:34]1[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=1[C:36]([NH:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]([CH:9]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[N:8][C:4]=2[CH:3]=1)=[O:37])([O-:33])=[O:32]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 118752-Nitrobenzoyl chlorideHCID 67351926ethyl 3-(5-amino-1H-benzimidazol-1-yl)-3-phenylpropanoate

Produkt 1

HCID 58653693Ethyl 3-{5-[(2-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of ethyl 3-(5-amino-1H-benzimidazol-1-yl)-3-phenylpropanoate (250 mg, 809 μmol) in dichloromethane (15 mL) was added triethylamine (250 μL, 1.78 mmol) and 2-nitrobenzoyl chloride (240 μL, 1.78 mmol). The solution was stirred at room temperature for 110 hours, and was then evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (97:3) to afford the title compound, [LCMS (Method A, Mobile Phase II) RT=5.23 min, MH+ 459].

Aufarbeitung

  1. customwas then evaporated in vacuo
  2. customThe residue was purified by flash column chromatography on silica gel
  3. washeluting with a mixture of dichloromethane and methanol (97:3)

Quellen und Nachweise

ORD-Eintrag
ord-23a1a169cef14f89af381a41822628dc
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003806B2

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