BROMINE CHLORIDE (BrCl) → HCID 178462081, compound

HRID 2054017Notes

Reaction equation

HRID 2054017 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([C:11]([NH:13][C@H:14]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:18]=3[N:17]=2)[CH3:15])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=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.[C:57]([O:61][C:62]([NH:64][CH2:65][CH:66]1[NH:70][CH2:69][CH2:68][S:67]1)=[O:63])([CH3:60])([CH3:59])[CH3:58].BrCl>CN(C)C=O.ClCCl.CO>[Br:1][C:2]1[CH:10]=[C:9]([CH:8]=[CH:7][C:3]=1[C:4]([N:70]1[CH2:69][CH2:68][S:67][CH:66]1[CH2:65][NH:64][C:62]([O:61][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:63])=[O:6])[C:11]([NH:13][C@H:14]([C:16]1[NH:20][C:19]2[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:18]=2[N:17]=1)[CH3:15])=[O:12]

Participants

8

Reactant 5

HCID 61697BROMINE CHLORIDE (BrCl)HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 45092297HCID 45092297, compoundHCID 178462082HCID 178462082, compound

Product 1

HCID 178462081HCID 178462081, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 1g from (1S)-2-bromo-4-{N-[1-(5-chloro-1H-benzimidazol-2-yl)ethyl]aminocarbonyl}benzoic acid, TBTU, diisopropylethylamine and rac.-2-(tert-butoxycarbonylaminomethyl)thiazolidine in dimethylformamide. Yield: 23%; Rf value: 0.52 (silica gel: dichloromethane/methanol/glacial acetic acid=9:1:0.1); C26H29BrClN5O4S (622.969); mass spectrum: (M−H)−=620/622/624 (bromo-chlorine isotope).

Sources & evidence

ORD record
ord-40e705a8fa204585b387b6c99e99841d
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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