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

HRID 1502475Notes

Reaction equation

HRID 1502475 reaction equation
[F:1][C:2]1[C:3]([CH3:27])=[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)=[C:10]([CH3:26])[N:9]=2)[CH:5]=[N:6][CH:7]=1.FC(F)(F)C(O)=O>ClCCCl>[F:1][C:2]1[C:3]([CH3:27])=[C:4]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH2:18])[N:14]=[CH:15]3)=[C:10]([CH3:26])[N:9]=2)[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67976737Tert-butyl 7-(5-fluoro-4-methylpyridin-3-yl)-5-methyl-2,6-naphthyridin-3-ylcarbamate

Product 1

HCID 679750717-(5-Fluoro-4-methylpyridin-3-yl)-5-methyl-2,6-naphthyridin-3-amineYield 99.4%

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)-5-methyl-2,6-naphthyridin-3-ylcarbamate (110 mg, 0.30 mmol) in 1,2-dichloroethane (2 mL) was treated with trifluoroacetic acid (0.23 mL, 3.0 mmol), and the mixture was stirred at 40° C. for 2 hours. The mixture was concentrated in vacuo and then diluted with dichloromethane (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 (80 mg, 99%), which was used in the next step without further purification.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with dichloromethane (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-bc7a6863168f4bd2b5536026e7471ce1
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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