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

HRID 468959
Notes
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Reaction equation

HRID 468959 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-91b4b036a19b4ecc9cae8b51ccd2b508
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08623889B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes