Trifluoroacetic acid → 1-Methyl-2-aminomethylbenzimidazol-5-yl-carboxylic acid-n-(2-pyridyl)-n-(2-ethoxycarbonylethyl)amide trifluoroacetate

HRID 50371Notes

Reaction equation

HRID 50371 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:8]([C:10]1[CH:28]=[CH:27][C:13]2[N:14]([CH3:26])[C:15]([CH2:17][NH:18]C(OC(C)(C)C)=O)=[N:16][C:12]=2[CH:11]=1)=[O:9].[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39]>C(Cl)Cl>[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:8]([C:10]1[CH:28]=[CH:27][C:13]2[N:14]([CH3:26])[C:15]([CH2:17][NH2:18])=[N:16][C:12]=2[CH:11]=1)=[O:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 184126741-Methyl-2-(n-tert-butoxycarbonylaminomethyl)benzimidazol-5-yl-carboxylic acid-n-(2-pyridyl)-n-(2-ethoxycarbonylethyl)amide

Product 1

HCID 184124831-Methyl-2-aminomethylbenzimidazol-5-yl-carboxylic acid-n-(2-pyridyl)-n-(2-ethoxycarbonylethyl)amide trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.81 g (0.10 mol) of 1-methyl-2-(N-tert-butoxycarbonylaminomethyl)benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide were dissolved in 25 mL of methylene chloride, mixed with 5 mL of trifluoroacetic acid and stirred for 5 hours at ambient temperature. Then the solvent was evaporated off and the residue was stirred with ether. The crystals thus formed were filtered off, washed with ether, and dried. Yield: 3.15 g (68% of theory), C20H23N5O3 (381.4); Rf value: 0.18 (silica gel; methylene chloride/ethanol=9:1).

Workup

  1. customThen the solvent was evaporated off
  2. stirringthe residue was stirred with ether
  3. customThe crystals thus formed
  4. filtrationwere filtered off
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-736ff238279d4cfb90a926dc0679e11a
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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