Chlorine → HCID 178462093, compound

HRID 2054068Notes

Reaction equation

HRID 2054068 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[N:9]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][C:11]=2[C:19]([F:22])([F:21])[F:20])[C:8]2[CH:23]=[CH:24][CH:25]=[CH:26][C:7]=2[N:6]=1)[CH3:3].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:58][C:59]1[CH:70]=[CH:69][C:62]2[NH:63][C:64]([C@@H:66]([NH2:68])[CH3:67])=[N:65][C:61]=2[CH:60]=1.ClCl>CS(C)=O.ClCCl.CO>[Cl:58][C:59]1[CH:70]=[CH:69][C:62]2[NH:63][C:64]([C@@H:66]([NH:68][C:14](=[O:16])[C:13]3[CH:17]=[CH:18][C:10]([N:9]4[C:8]5[CH:23]=[CH:24][CH:25]=[CH:26][C:7]=5[N:6]=[C:5]4[CH2:4][N:2]([CH3:3])[CH3:1])=[C:11]([C:19]([F:20])([F:22])[F:21])[CH:12]=3)[CH3:67])=[N:65][C:61]=2[CH:60]=1

Participants

8

Reactant 5

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 42034613(S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamineHCID 69314806HCID 69314806, compound

Product 1

HCID 178462093HCID 178462093, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 1g from 4-(2-dimethylaminomethylbenzimidazol-1-yl)-3-trifluoromethylbenzoic acid, TBTU, diisopropylethylamine, and (1S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamine in dimethylsulfoxide. Yield: 26%; Rf value: 0.25 (silica gel: dichloromethane/methanol=10:1); C27H24ClF3N6O (540.975); mass spectrum: (M+H)+=541/543 (chlorine isotope).

Sources & evidence

ORD record
ord-0012635f3b3646ccbed1a81b1dc6adca
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

Loading…