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

HRID 2053824Notes

Reaction equation

HRID 2053824 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[C:12]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13])[C:6]([OH:8])=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:52][C:53]1[CH:64]=[CH:63][C:56]2[NH:57][C:58]([CH:60]([NH2:62])[CH3:61])=[N:59][C:55]=2[CH:54]=1.ClCl>O1CCCC1.C(Cl)Cl.C(O)C>[Cl:52][C:53]1[CH:64]=[CH:63][C:56]2[NH:57][C:58]([CH:60]([NH:62][C:6](=[O:8])[C:5]3[CH:9]=[CH:10][C:11]([C:12]([N:14]4[CH2:18][CH2:17][CH2:16][CH2:15]4)=[O:13])=[C:3]([C:2]([F:1])([F:20])[F:19])[CH:4]=3)[CH3:61])=[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 69311101HCID 69311101, compoundHCID 178463384HCID 178463384, compound

Product 1

HCID 178464782Rac.-n-[1-(5-chloro-1h-benzimidazol-2-yl)]ethyl-3-trifluoromethyl-4-(pyrrolidin-1-ylcarbonyl)benzamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from 3-trifluoromethyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine and rac.-1-(5-chloro-1H-benzimidazol-2-yl)ethylamine in tetrahydrofuran. Yield: quantitative; Rf value: 0.50 (silica gel; methylene chloride/ethanol=9:1); C22H20ClF3N4O2 (464.88); mass spectrum: (M−H)-=463/465 (chlorine isotope).

Sources & evidence

ORD record
ord-0e927819867a42c1946d83d990f9947b
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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