Trifluoroacetic acid → 7-Chloro-2,6-naphthyridin-3-amine

HRID 1502416Notes

Reaction equation

HRID 1502416 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([NH:19]C(=O)OC(C)(C)C)[N:15]=[CH:16]2)=[CH:11][N:10]=1>ClC(Cl)C>[Cl:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([NH2:19])[N:15]=[CH:16]2)=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86674971Tert-butyl 7-chloro-2,6-naphthyridin-3-ylcarbamate

Product 1

HCID 866749727-Chloro-2,6-naphthyridin-3-amineYield 91.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Trifluoroacetic acid (0.43 mL, 5.5 mmol) was added to a solution of tert-butyl 7-chloro-2,6-naphthyridin-3-ylcarbamate (410 mg, 1.4 mmol) in dichloroethane (7 mL). After 4 hours, the reaction mixture was concentrated in vacuo, diluted with methylene chloride (50 mL), and washed with saturated aqueous sodium bicarbonate solution (20 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 4 g, ISCO, 0-100% ethyl acetate in heptane) to afford the title compound as a yellow solid (230 mg, 86%), which was used in the next step without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additiondiluted with methylene chloride (50 mL)
  3. washwashed with saturated aqueous sodium bicarbonate solution (20 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto afford a residue that
  9. customwas purified by flash chromatography (silica, 4 g, ISCO, 0-100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-75f02842bc244e949c940b972dfdd587
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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