Chlorine → Rac.-3-chloro-n-[1-(5-chloro-1h-benzimidazol-2-yl)ethyl]-4-[3-(2,2,2-trifluoroacetylamino)pyrrolidin-1-ylcarbonyl]benzamide

HRID 2053995Notes

Reaction equation

HRID 2053995 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]([NH:13][CH:14]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:18]=3[N:17]=2)[CH3:15])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[F:26][C:27]([F:37])([F:36])[C:28]([NH:30][CH:31]1[CH2:35][CH2:34][NH:33][CH2:32]1)=[O:29].C(N(C(C)C)CC)(C)C.ClCl>CS(C)=O>[Cl:1][C:2]1[CH:10]=[C:9]([CH:8]=[CH:7][C:3]=1[C:4]([N:33]1[CH2:34][CH2:35][CH:31]([NH:30][C:28](=[O:29])[C:27]([F:37])([F:36])[F:26])[CH2:32]1)=[O:6])[C:11]([NH:13][CH:14]([C:16]1[NH:20][C:19]2[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:18]=2[N:17]=1)[CH3:15])=[O:12]

Participants

6

Reactant 4

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 5375752,2,2-Trifluoro-N-(pyrrolidin-3-YL)acetamideHCID 178464831HCID 178464831, compound

Product 1

HCID 178464812Rac.-3-chloro-n-[1-(5-chloro-1h-benzimidazol-2-yl)ethyl]-4-[3-(2,2,2-trifluoroacetylamino)pyrrolidin-1-ylcarbonyl]benzamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Prepared analogously to Example 1d from rac.-2-chloro-4-{N-[1-(5-chloro-1H-benzimidazol-2-yl)ethyl]aminocarbonyl}benzoic acid, 3-(2,2,2-trifluoroacetylamino)pyrrolidine, PFTU, and diisopropylethylamine in DMSO at ambient temperature. HPLC-MS results: retention time: 4.34 minutes; C23H20Cl2F3N5O3 (542.34); mass spectrum: (M−H)−=541/543/545 (chlorine isotope).

Workup

  1. customHPLC-MS results

Sources & evidence

ORD record
ord-f53cfa2108744753ad7d027e81cfc0eb
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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