Chlorine → HCID 178427029, compound

HRID 2053760Notes

Reaction equation

HRID 2053760 reaction equation
[CH3:1][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:67]=[CH:66][C:53]2[N:54]=[C:55]([CH:57]([NH2:65])[CH2:58][C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)[NH:56][C:52]=2[CH:51]=1.ClCl>O1CCCC1.ClCCl.C(O)C>[Cl:49][C:50]1[CH:67]=[CH:66][C:53]2[NH:54][C:55]([CH:57]([NH:65][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][C:10]([C:11]([N:13]4[CH2:17][CH:16]=[CH:15][CH2:14]4)=[O:12])=[C:2]([CH3:1])[CH:3]=3)[CH2:58][C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)=[N:56][C:52]=2[CH:51]=1

Participants

8

Reactant 5

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 118586383-Methyl-4-(2,5-dihydropyrrol-1-ylcarbonyl)benzoic acidHCID 43114481HCID 43114481, compound

Product 1

HCID 178427029HCID 178427029, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from 3-methyl-4-(2,5-dihydropyrrol-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and rac.-1-(5-chlorobenzimidazol-2-yl)-2-phenylethylamine in tetrahydrofuran. Yield: 90%; Rf value: 0.52 (silica gel; dichloromethane/ethanol=9:1); C28H25ClN4O2 (484.99); mass spectrum: (M+H)+=485/487 (chlorine isotope).

Sources & evidence

ORD record
ord-62c27902a6c94df5895d07fce1b6eade
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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