Trifluoroacetic acid → HCID 69035893, compound

HRID 1930290Notes

Reaction equation

HRID 1930290 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C:9]1[CH:10]=[C:11]([C:16]2[C:17](=[O:38])[N:18]([CH2:36][CH3:37])[C:19]3[C:24]([CH:25]=2)=[CH:23][N:22]=[C:21]([NH:26]CC2C=CC(OC)=CC=2)[CH:20]=3)[CH:12]=[CH:13][C:14]=1[F:15].C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:26][C:21]1[CH:20]=[C:19]2[C:24]([CH:25]=[C:16]([C:11]3[CH:12]=[CH:13][C:14]([F:15])=[C:9]([NH2:8])[CH:10]=3)[C:17](=[O:38])[N:18]2[CH2:36][CH3:37])=[CH:23][N:22]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 69038831HCID 69038831, compound

Product 1

HCID 69035893HCID 69035893, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of TFA in CH2Cl2 (10%, 50 mL) was added 3-(3-amino-4-fluoro-phenyl)-1-ethyl-7-(4-methoxy-benzylamino)-1H-[1,6]naphthyridin-2-one (2.0 g, 4.78 mmol). The resulting mixture was stirred at 50° C. overnight. The reaction mixture was poured saturated aq NaHCO3 solution (100 mL), and was extracted with CH2Cl2 (3×75 mL). The combined organic layer was dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel column chromatography to give 7-amino-3-(3-amino-4-fluorophenyl)-1-ethyl-1,6-naphthyridin-2(1H)-one (0.45 g, 32% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.35 (s, 1 H), 7.76 (s, 1 H), 7.09 (dd, J=9.0, 2.1 Hz, 1 H), 6.97 (dd, J=11.4, 8.4 Hz, 1 H), 6.75 (m, 1 H), 6.44 (s, 2 H), 6.31 (s, 1 H), 5.09 (s, 2 H), 4.08 (q, J=7.2 Hz, 2 H), 1.20 (t, J=7.2 Hz, 3 H), MS (ESI) m/z (M+H+): 299.3.

Workup

  1. extractionwas extracted with CH2Cl2 (3×75 mL)
  2. dry with materialThe combined organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-adad3a4a04e64b11b8306eb7ce92eb64
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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