Chlorine → N-[(1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-hydroxyethyl]-4-(2,5-dihydropyrrol-1-ylcarbonyl)-3-trifluoromethylbenzamide

HRID 2054053Notes

Reaction equation

HRID 2054053 reaction equation
[N:1]1([C:6]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][C:9]=2[C:17]([F:20])([F:19])[F:18])=[O:7])[CH2:5][CH:4]=[CH:3][CH2:2]1.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:52][C:53]1[CH:65]=[CH:64][C:56]2[NH:57][C:58]([C@@H:60]([NH2:63])[CH2:61][OH:62])=[N:59][C:55]=2[CH:54]=1.ClCl>O1CCCC1.ClCCl.C(O)C>[Cl:52][C:53]1[CH:65]=[CH:64][C:56]2[NH:57][C:58]([C@@H:60]([NH:63][C:12](=[O:14])[C:11]3[CH:15]=[CH:16][C:8]([C:6]([N:1]4[CH2:2][CH:3]=[CH:4][CH2:5]4)=[O:7])=[C:9]([C:17]([F:20])([F:19])[F:18])[CH:10]=3)[CH2:61][OH:62])=[N:59][C:55]=2[CH:54]=1

Participants

8

Reactant 5

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 693126324-(2,5-Dihydropyrrol-1-ylcarbonyl)-3-trifluoromethylbenzoic acidHCID 178511833HCID 178511833, compound

Product 1

HCID 178523886N-[(1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-hydroxyethyl]-4-(2,5-dihydropyrrol-1-ylcarbonyl)-3-trifluoromethylbenzamideYield 20%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from 4-(2,5-dihydropyrrol-1-ylcarbonyl)-3-trifluoromethylbenzoic acid, TBTU, diisopropylethylamine, and (1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-hydroxyethylamine in tetrahydrofuran. Yield: 20%; Rf value: 0.43 (silica gel: dichloromethane/ethanol=9:1); C22H18ClF3N4O3 (478.856); mass spectrum: (M+H)+=479/481 (chlorine isotope).

Sources & evidence

ORD record
ord-ab81b4bfaa2a4eec9d5262f530b0416a
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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