Chlorine → HCID 178436689, compound

HRID 2053765Notes

Reaction equation

HRID 2053765 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[C:12]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13])[C:6]([OH:8])=O)#[CH:2].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:50][C:51]1[CH:62]=[CH:61][C:54]2[N:55]=[C:56]([CH:58]([NH2:60])[CH3:59])[NH:57][C:53]=2[CH:52]=1.ClCl>O1CCCC1.ClCCl.C(O)C>[Cl:50][C:51]1[CH:62]=[CH:61][C:54]2[NH:55][C:56]([CH:58]([NH:60][C:6](=[O:8])[C:5]3[CH:9]=[CH:10][C:11]([C:12]([N:14]4[CH2:18][CH2:17][CH2:16][CH2:15]4)=[O:13])=[C:3]([C:1]#[CH:2])[CH:4]=3)[CH3:59])=[N:57][C:53]=2[CH:52]=1

Participants

8

Reactant 5

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 242525581-(5-chloro-1H-1,3-benzodiazol-2-yl)ethan-1-amineHCID 85977055HCID 85977055, compound

Product 1

HCID 178436689HCID 178436689, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from 3-ethynyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and rac.-1-(5-chlorobenzimidazol-2-yl)ethylamine in tetrahydrofuran. Yield: 46%; Rf value: 0.48 (silica gel; dichloromethane/ethanol=9:1); C23H21ClN4O2 (420.90); mass spectrum: (M+H)+=421/423 (chlorine isotope).

Sources & evidence

ORD record
ord-8a490964d15a485684e905ddf9b6f8d8
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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