Trifluoroacetic acid → HCID 178511777, compound

HRID 2053769Notes

Reaction equation

HRID 2053769 reaction equation
C(OC([NH:8][C@H:9]([C:17]1[NH:21][C:20]2[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:19]=2[N:18]=1)[CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:26][C:24]1[CH:23]=[CH:22][C:20]2[NH:21][C:17]([C@@H:9]([NH2:8])[CH2:10][C:11]3[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=3)=[N:18][C:19]=2[CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454162HCID 178454162, compound

Product 1

HCID 178511777HCID 178511777, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.88 g (5.04 mmol) of (S)—N-tert-butoxycarbonyl-1-(5-chloro-1H-benzimidazol-2-yl)-2-(pyridin-4-yl)ethylamine is dissolved in 35 mL of dichloromethane and combined with 5 mL of trifluoroacetic acid. The mixture is stirred for 16 hours at ambient temperature and then the volatile constituents are distilled off. The residue is made alkaline with 2 molar sodium hydroxide solution, evaporated down and then digested with a little water and ethyl acetate. The crystals thus obtained are dried. Yield: 1.38 g (quantitative); Rf value: 0.09 (silica gel; dichloromethane/methanol=9:1); C14H13ClN4 (272.74); mass spectrum: (M+H)+=273/275 (chlorine isotope).

Workup

  1. distillationthe volatile constituents are distilled off
  2. customevaporated down
  3. customThe crystals thus obtained
  4. customare dried

Sources & evidence

ORD record
ord-ba719231ed2a4eb1a06c6d52509a5107
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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