Chlorine → HCID 178494052, compound

HRID 2054066Notes

Reaction equation

HRID 2054066 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[CH:10][N:11]([C:12]3[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][C:13]=3[C:21]([F:24])([F:23])[F:22])[C:7]=2[CH:6]=[CH:5][N:4]=1.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:56][C:57]1[CH:68]=[CH:67][C:60]2[NH:61][C:62]([C@@H:64]([NH2:66])[CH3:65])=[N:63][C:59]=2[CH:58]=1.ClCl>CS(C)=O.ClCCl.CO>[Cl:56][C:57]1[CH:68]=[CH:67][C:60]2[NH:61][C:62]([C@@H:64]([NH:66][C:16](=[O:18])[C:15]3[CH:19]=[CH:20][C:12]([N:11]4[C:7]5[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[C:8]=5[N:9]=[CH:10]4)=[C:13]([C:21]([F:22])([F:24])[F:23])[CH:14]=3)[CH3:65])=[N:63][C:59]=2[CH:58]=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 69312503HCID 69312503, compound

Product 1

HCID 178494052HCID 178494052, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 1g from 4-(4-methoxyimidazo[4,5-c]pyridin-1-yl)-3-trifluoromethylbenzoic acid, TBTU, diisopropylethylamine, and (1S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamine in dimethylsulfoxide. Yield: 46%; Rf value: 0.39 (silica gel: dichloromethane/methanol=10:1); C24H18ClF3N6O2 (514.893); mass spectrum: (M+H)+=515/517 (chlorine isotope).

Sources & evidence

ORD record
ord-b5d5b1e86ab7485488e129424a973e50
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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