Trifluoroacetic acid → HCID 178509976, compound

HRID 2053825Notes

Reaction equation

HRID 2053825 reaction equation
C(OC([NH:8][CH2:9][CH:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15]([C:17]1[CH:40]=[CH:39][C:20]([C:21]([NH:23][CH:24]([C:29]2[NH:33][C:32]3[CH:34]=[CH:35][C:36]([Cl:38])=[CH:37][C:31]=3[N:30]=2)[CH2:25][C:26]([NH2:28])=[O:27])=[O:22])=[CH:19][C:18]=1[Cl:41])=[O:16])=O)(C)(C)C.FC(F)(F)C(O)=O.ClCl>ClCCl.CO>[NH2:8][CH2:9][CH:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15]([C:17]1[CH:40]=[CH:39][C:20]([C:21]([NH:23][CH:24]([C:29]2[NH:33][C:32]3[CH:34]=[CH:35][C:36]([Cl:38])=[CH:37][C:31]=3[N:30]=2)[CH2:25][C:26]([NH2:28])=[O:27])=[O:22])=[CH:19][C:18]=1[Cl:41])=[O:16]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 24526ChlorineHCID 178453069HCID 178453069, compound

Product 1

HCID 178509976HCID 178509976, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 17 from 4-[2-(N-tert-butoxycarbonylaminomethyl)pyrrolidine-1-carbonyl]-N-[2-aminocarbonyl-1-(5-chloro-1H-benzimidazol-2-yl)ethyl]-3-chlorobenzamide and trifluoroacetic acid. Yield: 59% (mixture of all four stereoisomers); Rf value: 0.23 (silica gel; dichloromethane/methanol=7:3); C23H24Cl2N6O3 (503.39); mass spectrum: (M+H)+=503/505/507 (chlorine isotope).

Workup

  1. additionYield: 59% (mixture of all four stereoisomers)

Sources & evidence

ORD record
ord-c984bf4a132545cc915e7ee734ca9b7c
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

Loading…