Trifluoroacetic acid → HCID 69297968, compound

HRID 1930292Notes

Reaction equation

HRID 1930292 reaction equation
FC(F)(F)C(O)=O.COC1C=CC(C[NH:15][C:16]2[CH:25]=[C:24]3[C:19]([CH:20]=[C:21]([C:28]4[CH:33]=[C:32]([NH2:34])[C:31]([F:35])=[CH:30][C:29]=4[CH3:36])[C:22](=[O:27])[N:23]3[CH3:26])=[CH:18][N:17]=2)=CC=1>C(Cl)Cl>[NH2:15][C:16]1[CH:25]=[C:24]2[C:19]([CH:20]=[C:21]([C:28]3[CH:33]=[C:32]([NH2:34])[C:31]([F:35])=[CH:30][C:29]=3[CH3:36])[C:22](=[O:27])[N:23]2[CH3:26])=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69297513HCID 69297513, compound

Product 1

HCID 69297968HCID 69297968, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Trifluoroacetic acid (2 mL, 26.9 mmol) was added to a solution of 7-(4-methoxybenzylamino)-3-(5-amino-4-fluoro-2-methylphenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (0.8 g, 1.9 mmol) in DCM (10 mL) and the reaction mixture was refluxed at 50° C. for 2 hour. After cooling to RT, the reaction mixture was washed with water and the combined aqueous layers were neutralized with saturated aq NaHCO3 to pH 7-8. Then the aqueous layer was extracted with EtOAc (3×50 mL), the extracts were dried (Na2SO4) and concentrated to give 7-amino-3-(5-amino-4-fluoro-2-methylphenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (0.3 g, 53% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.29 (s, 1H), 7.57 (s, 1 H), 6.83 (d, J=12.4 Hz, 1 H), 6.56 (d, J=9.6 Hz, 1 H), 6.48 (s, 2 H), 6.24 (s, 1 H), 4.87 (s, 2 H), 3.45 (s, 3 H), 1.94 (s, 3 H); MS (ESI) m/z: 299.0 [M+H]+.

Workup

  1. temperatureAfter cooling to RT
  2. washthe reaction mixture was washed with water
  3. extractionThen the aqueous layer was extracted with EtOAc (3×50 mL)
  4. dry with materialthe extracts were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-338779c34cfb4819a8f79ff85f9da06d
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

Loading…