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

HRID 23911

Reaction equation

HRID 23911 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-5630fff3ee9e486f93c393d391562ff6
Source dataset
uspto-grants-2005_02
Patent number
US06855713B2

Linked notes

Loading…