Triethylamine → 2-[2-(4-Cyanophenyl)-ethyl]-1-methyl-benzimidazole-5-yl-carboxylic acid-[4-(3-phenyl-allyl)-piperazinyl]-amide

HRID 23911

Reaktionsgleichung

Reaktionsgleichung von HRID 23911
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([C:21](O)=[O:22])=[CH:20][C:13]=3[N:12]=2)=[CH:5][CH:4]=1)#[N:2].[C:24]1([CH:30]=[CH:31][CH2:32][N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([N:41](CC)CC)C.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.F[B-](F)(F)F>CN(C)C=O.C(OCC)(=O)C>[C:24]1([CH:30]=[CH:31][CH2:32][N:33]2[CH2:34][CH2:35][N:36]([NH:41][C:21]([C:19]3[CH:18]=[CH:17][C:14]4[N:15]([CH3:16])[C:11]([CH2:10][CH2:9][C:6]5[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=5)=[N:12][C:13]=4[CH:20]=3)=[O:22])[CH2:37][CH2:38]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 86803CinnamylpiperazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 15516402HCID 15516402, Verbindung

Produkt 1

HCID 697934992-[2-(4-Cyanophenyl)-ethyl]-1-methyl-benzimidazole-5-yl-carboxylic acid-[4-(3-phenyl-allyl)-piperazinyl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

0.4 g of 2-[2-(4-Cyanophenyl)-ethyl]-1-methyl-benzimidazole-5-yl-carboxylic acid (1.3 mmol), 4-(3-phenyl-allyl)-piperazine (0.26 g, 1.3 mmol) and 0.4 ml of triethylamine are dissolved in 8 ml of dimethylformamide. 0.54 g of O-(Benzotriazole-1-yl)-N,N,N′,N′-tetramethyluronium-tetrafluoroborate (═TBTU; 1.7 mmol) are added and stirred for 24 h at room temperature. After diluting with 20 ml of ethyl acetate, it is washed with saturated, aqueous sodium bicarbonate solution and with water, and dried over sodium sulphate. The solvent is boiled down and the product purified chromatographically (silica gel; gradient; acetic ester/methanol 100% in 60% acetic ester). Yield: 0.52 g (80%); yellow oil.

Aufarbeitung

  1. washis washed with saturated, aqueous sodium bicarbonate solution
  2. dry with materialwith water, and dried over sodium sulphate
  3. customthe product purified chromatographically (silica gel; gradient; acetic ester/methanol 100% in 60% acetic ester)

Quellen und Nachweise

ORD-Eintrag
ord-5630fff3ee9e486f93c393d391562ff6
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855713B2

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