Chlorine → HCID 178492725, compound

HRID 2054001Notes

Reaction equation

HRID 2054001 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH2:12][N:13]1[CH2:18][CH2:17][NH:16][C:15](=[O:19])[CH2:14]1)[C:6]([OH:8])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[Cl:51][C:52]1[CH:63]=[CH:62][C:55]2[NH:56][C:57]([C@@H:59]([NH2:61])[CH3:60])=[N:58][C:54]=2[CH:53]=1.ClCl>O1CCCC1.ClCCl.C(O)C>[Cl:51][C:52]1[CH:63]=[CH:62][C:55]2[NH:56][C:57]([C@@H:59]([NH:61][C:6](=[O:8])[C:5]3[CH:9]=[CH:10][C:11]([CH2:12][N:13]4[CH2:18][CH2:17][NH:16][C:15](=[O:19])[CH2:14]4)=[C:3]([O:2][CH3:1])[CH:4]=3)[CH3:60])=[N:58][C:54]=2[CH:53]=1

Participants

8

Reactant 5

HCID 24526Chlorine2×HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 42034613(S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamineHCID 693153843-Methoxy-4-(3-oxopiperazin-1-ylmethyl)benzoic acid

Product 1

HCID 178492725HCID 178492725, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from 3-methoxy-4-(3-oxopiperazin-1-ylmethyl)benzoic acid, TBTU, diisopropylethylamine and (1S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamine in tetrahydrofuran. Yield: 35%; Rf value: 0.39 (silica gel; dichloromethane/ethanol=4:1); C22H24ClN5O3 (441.92); mass spectrum: (M+H)+=442/444 (chlorine isotope) and (M−H)-=440/442 (chlorine isotope).

Sources & evidence

ORD record
ord-e665175ed82d45849c24538492eea2c5
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

Loading…