Trifluoroacetic acid → 3-(2-Aminoethyl)-5-chloropyridine 1-oxide

HRID 1749470Notes

Reaction equation

HRID 1749470 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11]1[CH:12]=[N+:13]([O-:18])[CH:14]=[C:15]([Cl:17])[CH:16]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[N+:13]([O-:18])[CH:14]=[C:15]([Cl:17])[CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 1181621543-(2-((tert-Butoxycarbonyl)amino)ethyl)-5-chloropyridine 1-oxide

Product 1

HCID 1181621313-(2-Aminoethyl)-5-chloropyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-((tert-butoxycarbonyl)amino)ethyl)-5-chloropyridine 1-oxide (90 mg, crude) in DCM (3 mL) was added TFA (1.5 mL) at 0° C. The resulting reaction mixture was stirred at room temperature for 1.5 h. The reaction mixture was concentrated to afford the crude title product, which was used directly in the next step without further purification (80 mg, crude). MS (ESI) m/z 173.1 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-dbeae91f70fa424f9520f5e46384c33f
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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