Triethylamine → 3-chloro-N-(5-chloro-1H-benzimidazol-2-ylmethyl)-4-(2-methylpyrrolidin-1-ylcarbonyl)benzamide

HRID 2053794Notes

Reaction equation

HRID 2053794 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[C:22](O)=[O:23])[C:5]([NH:7][CH2:8][C:9]1[NH:13][C:12]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:11]=2[N:10]=1)=[O:6].[CH3:25][CH:26]1[CH2:30][CH2:29][CH2:28][NH:27]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[C:22]([N:27]1[CH2:28][CH2:29][CH2:30][CH:26]1[CH3:25])=[O:23])[C:5]([NH:7][CH2:8][C:9]1[NH:13][C:12]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:11]=2[N:10]=1)=[O:6]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 130032-MethylpyrrolidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178523088HCID 178523088, compound

Product 1

HCID 1784262083-chloro-N-(5-chloro-1H-benzimidazol-2-ylmethyl)-4-(2-methylpyrrolidin-1-ylcarbonyl)benzamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Prepared analogously to Example 1d from 3-chloro-N-(5-chloro-1H-benzimidazol-2-ylmethyl)-4-carboxybenzamide, 2-methylpyrrolidine, TBTU, and triethylamine in DMSO at ambient temperature. HPLC-MS results: retention time: 3.62 minutes; C21H20Cl2N4O2 (431.32); mass spectrum: (M+H)+=431.2.

Workup

  1. customHPLC-MS results

Sources & evidence

ORD record
ord-adc23b08523e4560ab7dbe14e974fb93
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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