Diisopropylethylamine → HCID 178523883, compound

HRID 2054098Notes

Reaction equation

HRID 2054098 reaction equation
Br[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: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.[Cl:65]Cl>O1CCCC1>[Cl:65][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:60][C@H:57]([C:55]1[NH:54][C:53]2[CH:61]=[CH:62][C:50]([Br:49])=[CH:51][C:52]=2[N:56]=1)[CH2:58][OH:59])=[O:7]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 693098653-Bromo-4-(2,5-dihydropyrrol-1-ylcarbonyl)benzoic acidHCID 131726752Bromine chlorineHCID 178511832(1R)-1-(5-bromo-1H-benzimidazol-2-yl)-2-hydroxyethylamine

Product 1

HCID 178523883HCID 178523883, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to Example 1g from 3-bromo-4-(2,5-dihydropyrrol-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and (1R)-1-(5-bromo-1H-benzimidazol-2-yl)-2-hydroxyethylamine in tetrahydrofuran. Yield: 57%; melting point: 124° C.-126° C.; C21H18BrClN4O3 (489.76); mass spectrum: (M+H)+=489/491/493 (bromine/chlorine isotope).

Sources & evidence

ORD record
ord-84d5f502de794f1084e9d6e0d1468bb6
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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