Trifluoroacetic acid → HCID 69480984, compound

HRID 2364308Notes

Reaction equation

HRID 2364308 reaction equation
FC(F)(F)C(O)=O.CC(OC([NH:15][CH2:16][CH2:17][NH:18][C:19]1[C:20]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[N:21][CH:22]=[C:23]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH:24]=1)=O)(C)C>ClCCl>[NH2:15][CH2:16][CH2:17][NH:18][C:19]1[C:20]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[N:21][CH:22]=[C:23]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69481022HCID 69481022, compound

Product 1

HCID 69480984HCID 69480984, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of dichloromethane (2 mL) and trifluoroacetic acid (2 mL) was added ethyl 3-{[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]amino}-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate. The reaction mixture was stirred at room temperature for 3 hours, then concentrated in vacuo. The crude residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic layer was washed with water and brine, then dried over sodium sulfate. Filtration and concentration provided ethyl 3-[(2-aminoethyl)amino]-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.77 (s, 1 H), 7.72 (t, J=5.8 Hz, 1 H), 7.06 (dd, J=8.4, 5.4 Hz, 2 H), 6.90 (t, J=8.7 Hz, 2 H), 6.81 (s, 1 H), 6.63 (br, 2 H), 4.27 (q, J=7.1 Hz, 2 H), 3.79 (s, 2 H), 3.45 (m, 2 H), 3.08 (m, 2 H), 1.29 (t, J=7.2 Hz, 3 H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-517627d899d24abdaf6809d190eea88b
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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