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

HRID 1676046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1676046
[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:35]=[C:36]([CH:40]=[CH:41][CH:42]=1)[C:37](Cl)=[O:38])([O-:33])=[O:32]>ClCCl.CN(C1C=CN=CC=1)C>[N+:31]([C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=1)[C:37]([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:38])([O-:33])=[O:32]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-HCID 67351926ethyl 3-(5-amino-1H-benzimidazol-1-yl)-3-phenylpropanoate

Produkt 1

HCID 58653703Ethyl 3-{5-[(3-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 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 (280 μL, 2.03 mmol), 3-nitrobenzoyl chloride (375 mg, 2.03 mmol) and DMAP (10 mg, 81 μmol). The solution was stirred at room temperature for 144 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=5.53 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-1f2b334afdb14c05a09ec1f7899c39ba
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003806B2

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