Triethylamine → Ethyl 3-{5-[(4-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

HRID 1676041Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1676041
[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][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1)([O-:33])=[O:32]>ClCCl>[N+:31]([C:34]1[CH:35]=[CH:36][C:37]([C:38]([NH:1][C:2]2[CH:23]=[CH:22][C:5]3[N:6]([CH:9]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[N:8][C:4]=3[CH:3]=2)=[O:39])=[CH:41][CH:42]=1)([O-:33])=[O:32]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 67351926ethyl 3-(5-amino-1H-benzimidazol-1-yl)-3-phenylpropanoate

Produkt 1

HCID 58653626Ethyl 3-{5-[(4-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 (100 mg, 324 μmol) in dichloromethane (6 mL) was added triethylamine (100 μL, 710 μmol) and 4-nitrobenzoyl chloride (132 mg, 712 μmol). The solution was stirred at room temperature for 96 hours, and was evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with dichloromethane and methanol (97:3) to afford the title compound, [LCMS (Method A, Mobile Phase I) RT=4.92 min, MH+ 459].

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ffa5f2921d794e12ba3764a080055e4d
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003806B2

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