BROMINE CHLORIDE (BrCl) → HCID 178495735, compound

HRID 2053941Notes

Reaction equation

HRID 2053941 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12])[C:5]([OH:7])=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.[Cl:49][C:50]1[CH:63]=[CH:62][C:53]2[NH:54][C:55]([C@@H:57]([NH2:61])[CH2:58][O:59][CH3:60])=[N:56][C:52]=2[CH:51]=1.BrCl>CN(C)C=O.ClCCl.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12])[C:5]([NH:61][C@H:57]([C:55]1[NH:54][C:53]2[CH:62]=[CH:63][C:50]([Cl:49])=[CH:51][C:52]=2[N:56]=1)[CH2:58][O:59][CH3:60])=[O:7]

Participants

8

Reactant 5

HCID 61697BROMINE CHLORIDE (BrCl)HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 693124883-Bromo-4-(pyrrolidin-1-ylcarbonyl)benzoic acidHCID 178495727HCID 178495727, compound

Product 1

HCID 178495735HCID 178495735, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 1g from 3-bromo-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and (1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxyethylamine in dimethylformamide. Yield: 85%; Rf value: 0.60 (silica gel; dichloromethane/methanol=95:5); C22H22BrClN4O3 (505.80); mass spectrum: (M+H)+=503/505/507 (bromo-chlorine isotope).

Sources & evidence

ORD record
ord-207b5df0a4f041c589eed781e0621f22
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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