BROMINE CHLORIDE (BrCl) → HCID 178462054, compound

HRID 2054031Notes

Reaction equation

HRID 2054031 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.[Br:49][C:50]1[CH:61]=[CH:60][C:53]2[NH:54][C:55]([C@@H:57]([NH2:59])[CH3:58])=[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:59][C@H:57]([C:55]1[NH:54][C:53]2[CH:60]=[CH:61][C:50]([Br:49])=[CH:51][C:52]=2[N:56]=1)[CH3:58])=[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 178461853HCID 178461853, compound

Product 1

HCID 178462054HCID 178462054, compoundYield 72%

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-bromo-1H-benzimidazol-2-yl)ethylamine in tetrahydrofuran. Yield: 72%; Rf value: 0.50 (silica gel: dichloromethane/ethanol=9:1); C21H18Br2N4O2 (518.207); mass spectrum: (M+H)+=517/519/521 (bromo-chlorine isotope).

Sources & evidence

ORD record
ord-94198bff9a0e454eaa8fcb6149602c48
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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