Trifluoroacetic acid → 7-(5-Fluoro-4-methylpyridin-3-yl)-2,6-naphthyridin-3-amine

HRID 468956Notes

Reaction equation

HRID 468956 reaction equation
[F:1][C:2]1[C:3]([CH3:26])=[C:4]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH:18]C(=O)OC(C)(C)C)[N:14]=[CH:15]3)=[CH:10][N:9]=2)[CH:5]=[N:6][CH:7]=1.FC(F)(F)C(O)=O>ClCCCl>[F:1][C:2]1[C:3]([CH3:26])=[C:4]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH2:18])[N:14]=[CH:15]3)=[CH:10][N:9]=2)[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71115017Tert-butyl 7-(5-fluoro-4-methylpyridin-3-yl)-2,6-naphthyridin-3-ylcarbamate

Product 1

HCID 679743607-(5-Fluoro-4-methylpyridin-3-yl)-2,6-naphthyridin-3-amineYield 101.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

A suspension of tert-butyl 7-(5-fluoro-4-methylpyridin-3-yl)-2,6-naphthyridin-3-ylcarbamate (50 mg, 0.14 mmol) in 1,2-dichloroethane (1 mL) was treated with trifluoroacetic acid (0.11 mL, 1.41 mmol), and the mixture was stirred at 40° C. for 3 hours. The mixture was concentrated in vacuo and then diluted with ethyl acetate (50 mL) and washed with saturated aqueous sodium bicarbonate solution (10 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford the title compound as a bright yellow solid (36 mg, 98%), which was used in the next step without further purification.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with ethyl acetate (50 mL)
  3. washwashed with saturated aqueous sodium bicarbonate solution (10 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-67d8f3b80bec45f8ad3bb84f90eadc50
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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