Chlorine → HCID 178427081, compound

HRID 2053858Notes

Reaction equation

HRID 2053858 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][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.C([O:56][C:57]([CH2:59][CH2:60][CH:61]([NH2:72])[C:62]1[NH:66][C:65]2[CH:67]=[CH:68][C:69]([Cl:71])=[CH:70][C:64]=2[N:63]=1)=[O:58])C1C=CC=CC=1.ClCl>CS(C)=O.[OH-].[Na+].C(OCC)(=O)C.C(O)(=O)C>[Cl:71][C:69]1[CH:68]=[CH:67][C:65]2[NH:66][C:62]([CH:61]([NH:72][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][C:10]([C:11]([N:13]4[CH2:17][CH2:16][CH2:15][CH2:14]4)=[O:12])=[C:2]([CH3:1])[CH:3]=3)[CH2:60][CH2:59][C:57]([OH:58])=[O:56])=[N:63][C:64]=2[CH:70]=1

Participants

9

Reactant 5

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 120686863-Methyl 4-(pyrrolidin-1-ylcarbonyl)benzoic acidHCID 178511063HCID 178511063, compound

Product 1

HCID 178427081HCID 178427081, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 14798Sodium HydroxideSolventHCID 22609514Ethyl acetate acetateSolvent

Procedure

Prepared analogously to Example 1g from 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, 3-benzyloxycarbonyl-1-(5-chloro-1H-benzimidazol-2-yl)propylamine in dimethylsulfoxide and sodium hydroxide solution. Yield: 53%; Rf value: 0.16 (silica gel; ethyl acetate/acetic acid=95:5); C24H25ClN4O4 (468.94); mass spectrum: (M+H)+=469/471 (chlorine isotope).

Sources & evidence

ORD record
ord-8e8c707abdee4180bc6dd7101a713de5
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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