Chlorine → N-[1-(5-chloro-1H-benzimidazol-2-yl)ethyl]-3-chloro-4-(3-oxopiperazin-1-ylcarbonyl)benzamide

HRID 2053819Notes

Reaction equation

HRID 2053819 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[C:22](O)=[O:23])[C:5]([NH:7][CH2:8][C:9]1[NH:13][C:12]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:11]=2[N:10]=1)=[O:6].[CH3:25]N(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[O:56]=[C:57]1[CH2:62][NH:61][CH2:60][CH2:59][NH:58]1.ClCl>O1CCCC1.C(Cl)Cl.C(O)C>[Cl:18][C:16]1[CH:15]=[CH:14][C:12]2[NH:13][C:9]([CH:8]([NH:7][C:5](=[O:6])[C:4]3[CH:19]=[CH:20][C:21]([C:22]([N:61]4[CH2:60][CH2:59][NH:58][C:57](=[O:56])[CH2:62]4)=[O:23])=[C:2]([Cl:1])[CH:3]=3)[CH3:25])=[N:10][C:11]=2[CH:17]=1

Participants

8

Reactant 5

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 231360Piperazin-2-oneHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178523088HCID 178523088, compound

Product 1

HCID 178464815N-[1-(5-chloro-1H-benzimidazol-2-yl)ethyl]-3-chloro-4-(3-oxopiperazin-1-ylcarbonyl)benzamideYield 36%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1d from 3-chloro-N-(5-chloro-1H-benzimidazol-2-ylmethyl)-4-hydroxycarbonylbenzamide, TBTU, diisopropylethylamine, and 2-oxopiperazine in tetrahydrofuran. Yield: 36%; Rf value: 0.75 (silica gel; methylene chloride/ethanol=4:1); C21H19Cl2N5O3 (460.32); mass spectrum: (M+H)+=460/462/464 (chlorine isotope).

Sources & evidence

ORD record
ord-08eda446ab214191b01f210f15dfcf7a
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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