Chlorine → HCID 178462096, compound

HRID 2054069Notes

Reaction equation

HRID 2054069 reaction equation
[O:1]=[C:2]1[C:7]2[N:8]=[CH:9][N:10]([C:11]3[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][C:12]=3[C:20]([F:23])([F:22])[F:21])[C:6]=2[CH:5]=[CH:4][NH:3]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:55][C:56]1[CH:67]=[CH:66][C:59]2[NH:60][C:61]([C@@H:63]([NH2:65])[CH3:64])=[N:62][C:58]=2[CH:57]=1.ClCl>CS(C)=O.ClCCl.CO>[Cl:55][C:56]1[CH:67]=[CH:66][C:59]2[NH:60][C:61]([C@@H:63]([NH:65][C:15](=[O:16])[C:14]3[CH:18]=[CH:19][C:11]([N:10]4[C:6]5[CH:5]=[CH:4][NH:3][C:2](=[O:1])[C:7]=5[N:8]=[CH:9]4)=[C:12]([C:20]([F:21])([F:22])[F:23])[CH:13]=3)[CH3:64])=[N:62][C:58]=2[CH:57]=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 69311361HCID 69311361, compound

Product 1

HCID 178462096HCID 178462096, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 1g from 4-(4-oxo-4,5-dihydroimidazo[4,5-c]pyridin-1-yl)-3-trifluoromethylbenzoic acid, TBTU, diisopropylethylamine, and (1S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamine in dimethylsulfoxide. Yield: 51%; Rf value: 0.16 (silica gel: dichloromethane/methanol=10:1); C23H16ClF3N6O2 (500.866); mass spectrum: (M+H)+=501/503 (chlorine isotope).

Sources & evidence

ORD record
ord-e81aef95ac6847438da48896194fa74a
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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