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

HRID 2053822Notes

Reaction equation

HRID 2053822 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:61]=[CH:60][C:53]2[N:54]=[C:55]([C@@H:57]([NH2:59])[CH3:58])[NH:56][C:52]=2[CH:51]=1.ClCl>O1CCCC1.C(Cl)Cl.C(O)C>[Cl:49][C:50]1[CH:61]=[CH:60][C:53]2[NH:54][C:55]([C@@H:57]([NH:59][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)[CH3:58])=[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 42034613(S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamine

Product 1

HCID 178427139(S)-N-[1-(5-chloro-1H-benzimidazol-2-yl)]ethyl-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamideYield 76%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and (S)-1-(5-chlorobenzimidazol-2-yl)ethylamine in tetrahydrofuran. Yield: 76%; Rf value: 0.50 (silica gel; methylene chloride/ethanol=9:1); C22H23ClN4O2 (410.91); mass spectrum: (M−H)−=409/411 (chlorine isotope).

Sources & evidence

ORD record
ord-9121e496490e42a5b8ccf2900df6d63d
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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