BROMINE CHLORIDE (BrCl) → HCID 178448328, compound

HRID 2054023Notes

Reaction equation

HRID 2054023 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][CH:16]=[CH: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][CH2:59][CH3:60])=[N:56][C:52]=2[CH:51]=1.BrCl>O1CCCC1.ClCCl.C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([N:13]1[CH2:17][CH:16]=[CH: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][CH2:59][CH3:60])=[O:7]

Participants

8

Reactant 5

HCID 61697BROMINE CHLORIDE (BrCl)HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 693098653-Bromo-4-(2,5-dihydropyrrol-1-ylcarbonyl)benzoic acidHCID 178448311HCID 178448311, compound

Product 1

HCID 178448328HCID 178448328, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from 3-bromo-4-(2,5-dihydropyrrol-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and (1S)-1-(5-chloro-1H-benzimidazol-2-yl)butylamine in tetrahydrofuran. Yield: quantitative; Rf value: 0.57 (silica gel: dichloromethane/ethanol=9:1); C23H22BrClN4O2 (501.814); mass spectrum: (M+H)+=501/503/505 (bromo-chlorine isotope).

Sources & evidence

ORD record
ord-bfc12f83164246318f300330cdb73bca
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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