Chlorine → HCID 178426995, compound

HRID 2053878Notes

Reaction equation

HRID 2053878 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.[Cl:49][C:50]1[CH:67]=[CH:66][C:53]2[NH:54][C:55]([CH:57]([NH2:65])[C:58]3[CH:63]=[CH:62][CH:61]=[C:60]([Cl:64])[CH:59]=3)=[N:56][C:52]=2[CH:51]=1.ClCl>O1CCCC1.ClCCl.CO>[Cl:49][C:50]1[CH:67]=[CH:66][C:53]2[NH:54][C:55]([CH:57]([C:58]3[CH:63]=[CH:62][CH:61]=[C:60]([Cl:64])[CH:59]=3)[NH:65][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)=[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 120686863-Methyl 4-(pyrrolidin-1-ylcarbonyl)benzoic acidHCID 178509757HCID 178509757, compound

Product 1

HCID 178426995HCID 178426995, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 1g from 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and C-(5-chloro-1H-benzimidazol-2-yl)-C-(3chlorophenyl)methylamine in tetrahydrofuran. Yield: 48%; Rf value: 0.33 (silica gel; dichloromethane/methanol=20:1); C27H24C12N4O2 (507.42); mass spectrum: (M+H)+=507/509/511 (chlorine isotope).

Sources & evidence

ORD record
ord-efb44002a148486490a15cf7646114da
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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