Diisopropylethylamine → 3-bromo-N-[(1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-hydroxyethyl]-4-(pyrrolidin-1-ylcarbonyl)benzamide

HRID 2054002Notes

Reaction equation

HRID 2054002 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:62]=[CH:61][C:53]2[NH:54][C:55]([C@@H:57]([NH2:60])[CH2:58][OH:59])=[N:56][C:52]=2[CH:51]=1.BrBr.ClCl>O1CCCC1.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:60][C@H:57]([C:55]1[NH:54][C:53]2[CH:61]=[CH:62][C:50]([Cl:49])=[CH:51][C:52]=2[N:56]=1)[CH2:58][OH:59])=[O:7]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 693124883-Bromo-4-(pyrrolidin-1-ylcarbonyl)benzoic acidHCID 131726752Bromine chlorineHCID 178511833HCID 178511833, compound

Product 1

HCID 1785238853-bromo-N-[(1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-hydroxyethyl]-4-(pyrrolidin-1-ylcarbonyl)benzamideYield 90%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 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-hydroxyethylamine in tetrahydrofuran. Yield: 90%; Rf value: 0.40 (silica gel: dichloromethane/methanol=9:1); C21H20BrClN4O3 (491.77); mass spectrum: (M+H)+=491/493/495 (bromine/chlorine isotope).

Sources & evidence

ORD record
ord-fd5cfc056bc14f0b98a676c7cf475092
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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