Trifluoroacetic acid → HCID 69038373, compound

HRID 1257150Notes

Reaction equation

HRID 1257150 reaction equation
C(O)(C(F)(F)F)=O.COC1C=CC(C[NH:15][C:16]2[CH:25]=[C:24]3[C:19]([CH:20]=[C:21]([C:29]4[CH:34]=[C:33]([NH2:35])[C:32]([F:36])=[CH:31][C:30]=4[CH3:37])[C:22](=[O:28])[N:23]3[CH2:26][CH3:27])=[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:29]3[CH:34]=[C:33]([NH2:35])[C:32]([F:36])=[CH:31][C:30]=3[CH3:37])[C:22](=[O:28])[N:23]2[CH2:26][CH3:27])=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86713622HCID 86713622, compound

Product 1

HCID 69038373HCID 69038373, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

TFA (2 mL, 26.9 mmol) was added to a solution of 7-(4-methoxybenzylamino)-3-(5-amino-4-fluoro-2-methylphenyl)-1-ethyl-1,6-naphthyridin-2(1H)-one in DCM (10 mL) and the reaction mixture was refluxed at 50° C. for 2 h. After cooling to RT, the reaction mixture was washed with water and the combined aqueous layers were neutralized with satd. NaHCO3. The aqueous layer was extracted with EtOAc (3×) and the extracts were dried (Na2SO4) and concentrated to give 7-amino-3-(5-amino-4-fluoro-2-methylphenyl)-1-ethyl-1,6-naphthyridin-2(1H)-one (0.9 g, 46% yield, over 2 steps). 1H NMR (300 MHz, DMSO-d6): δ 8.30 (s, 1H), 7.56 (s, 1H), 6.83 (d, J=12.3 Hz, 1H), 6.57 (d, J=9.6 Hz, 1H), 6.40 (s, 2H), 6.32 (s, 1H), 4.85 (s, 2H), 4.07 (q, J=6.9 Hz, 2H), 1.94 (s, 3H), 1.19 (t, J=6.9 Hz, 3H); MS (ESI) m/z: 313.3 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-7036da4802b14afbaf420b4a9d55cf06
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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