Trifluoroacetic acid → 7-(4-Methylpyridin-3-yl)-2,6-naphthyridin-3-amine

HRID 468963Notes

Reaction equation

HRID 468963 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([NH:18]C(=O)OC(C)(C)C)[N:14]=[CH:15]2)=[CH:10][N:9]=1.FC(F)(F)C(O)=O>ClCCCl>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([NH2:18])[N:14]=[CH:15]2)=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71115140Tert-butyl 7-(4-methylpyridin-3-yl)-2,6-naphthyridin-3-ylcarbamate

Product 1

HCID 711150517-(4-Methylpyridin-3-yl)-2,6-naphthyridin-3-amineYield 99.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

A suspension of tert-butyl 7-(4-methylpyridin-3-yl)-2,6-naphthyridin-3-ylcarbamate (190 mg, 0.565 mmol) in DCE (3 mL) was treated with trifluoroacetic acid (0.437 mL, 5.65 mmol) and the mixture was stirred at 40° C. for 3 hours. The reaction 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 (133 mg, 99%), which was used without further purification.

Workup

  1. concentrationThe reaction 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-6e22ccca20c54301a3a03bcc79c18cac
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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