Trifluoroacetic acid → 5-[(2-Methoxy-ethylamino)-methyl]-pyridin-3-ylamine

HRID 55891Notes

Reaction equation

HRID 55891 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([CH2:14][NH:15][CH2:16][CH2:17][O:18][CH3:19])[CH:13]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:19][O:18][CH2:17][CH2:16][NH:15][CH2:14][C:12]1[CH:13]=[C:8]([NH2:7])[CH:9]=[N:10][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90356563{5-[(2-Methoxy-ethylamino)-methyl]-pyridin-3-yl}-carbamic acid tert-butyl ester

Product 1

HCID 890526115-[(2-Methoxy-ethylamino)-methyl]-pyridin-3-ylamineYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 56 (0.4 g, 1.42 mmol) in DCM (3 mL) was added TFA (3 mL) at 0° C. and stirred at rt for 3 h. The reaction mixture was concentrated, the residue was dissolved in MeOH, basified with Ambersep 900-OH resin, filtered to separate the resin and the filtrate concentrated to obtain the desired amine (90 mg, 88%) as a brown color viscous liquid. Rf: 0.1 (10% MeOH/CHCl3); (m/z):182 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 7.77 (1H, d, J=2.4 Hz), 7.66 (1H, d, J=1.6 Hz), 6.86 (1H, d, J=2 Hz), 5.19 (2H, m), 3.66 (2H, s), 3.39-3.36 (3H, m), 3.22 (3H, s), 2.62-2.59 (2H, m), 1.93-1.92 (1H, br s).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in MeOH
  3. filtrationfiltered
  4. customto separate the resin
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-92404279e56c4651a806a8606ac8ab9e
Source dataset
uspto-grants-2016_09
Patent number
US09433622B2

Reaction notes

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