Chlorine → HCID 178462092, compound

HRID 2054070Notes

Reaction equation

HRID 2054070 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[N:6]([C:14]2[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][C:15]=2[C:23]([F:26])([F:25])[F:24])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[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:18](=[O:19])[C:17]3[CH:21]=[CH:22][C:14]([N:6]4[C:7]5[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=5)[CH:13]=[C:5]4[CH2:4][N:2]([CH3:3])[CH3:1])=[C:15]([C:23]([F:25])([F:26])[F:24])[CH:16]=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 69315293HCID 69315293, compound

Product 1

HCID 178462092HCID 178462092, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 1g from 4-(2-dimethylaminomethyl-indol-1-yl)-3-trifluoromethylbenzoic acid, TBTU, diisopropylethylamine, and (1S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamine in dimethylsulfoxide. Yield: 37%; Rf value: 0.36 (silica gel: dichloromethane/methanol=10:1); C28H25ClF3N5O (539.987); mass spectrum: (M+H)+=540/542 (chlorine isotope).

Sources & evidence

ORD record
ord-8344dce98f8f4ec697d86e0a8a706b8c
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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