Tetrahydrofuran → N-[1-(5-chloro-1H-benzimidazol-2-yl)-5-benzyloxycarbonylaminopentyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide

HRID 2053818Notes

Reaction equation

HRID 2053818 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:21]([O:25]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH:40](N(C(C)C)CC)([CH3:42])[CH3:41].[Cl:49][C:50]1[CH:75]=[CH:74][C:53]2[NH:54][C:55]([CH:57]([NH2:73])[CH2:58][CH2:59][CH2:60][CH:61]([NH2:72])C(OCC3C=CC=CC=3)=O)=[N:56][C:52]=2[CH:51]=1.ClCl.[O:78]1[CH2:82][CH2:81][CH2:80][CH2:79]1>C(Cl)Cl.C(O)C>[Cl:49][C:50]1[CH:75]=[CH:74][C:53]2[NH:54][C:55]([CH:57]([NH:73][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)[CH2:58][CH2:59][CH2:60][CH2:61][NH:72][C:21]([O:78][CH2:82][C:81]3[CH:42]=[CH:40][CH:41]=[CH:79][CH:80]=3)=[O:25])=[N:56][C:52]=2[CH:51]=1

Participants

8

Reactant 6

HCID 8028TetrahydrofuranHCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 120686863-Methyl 4-(pyrrolidin-1-ylcarbonyl)benzoic acidHCID 178511003HCID 178511003, compound

Product 1

HCID 178427072N-[1-(5-chloro-1H-benzimidazol-2-yl)-5-benzyloxycarbonylaminopentyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and 1-(5-chloro-1H-benzimidazol-2-yl)-5-benzyloxycarbonyl-aminopentylamine in tetrahydrofuran. Yield: quantitative; Rf value: 0.52 (silica gel; methylene chloride/ethanol=9:1); C33H36ClN5O4 (602.13); mass spectrum: (M−H)−=600/602 (chlorine isotope).

Sources & evidence

ORD record
ord-e9cdda4663964543a35e05486e8dc419
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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