Trifluoroacetic acid → HCID 69096290, compound

HRID 1930294Notes

Reaction equation

HRID 1930294 reaction equation
COC1C=CC([CH2:7][N:8](C)[C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([C:21]4[CH:26]=[C:25]([NH2:27])[C:24]([F:28])=[CH:23][C:22]=4[Cl:29])[C:15](=[O:20])[N:16]3[CH3:19])=[CH:11][N:10]=2)=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:27][C:25]1[C:24]([F:28])=[CH:23][C:22]([Cl:29])=[C:21]([C:14]2[C:15](=[O:20])[N:16]([CH3:19])[C:17]3[C:12]([CH:13]=2)=[CH:11][N:10]=[C:9]([NH:8][CH3:7])[CH:18]=3)[CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69296325HCID 69296325, compound

Product 1

HCID 69096290HCID 69096290, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-2-chloro-4-fluorophenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (3 g, 6.6 mmol) in CH2Cl2 (50 mL) was treated with TFA (20 mL) and the mixture was heated to reflux overnight. The mixture was concentrated under reduced pressure, the residue was dissolved in 10% aq. of HCl (50 mL) and the aqueous layer was washed with EtOAc. The aqueous layer was neutralized with NaHCO3 aq. solution to pH 8, and then extracted with EtOAc (3×50 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated in vacuo to give 3-(5-amino-2-chloro-4-fluorophenyl)-1-methyl-7-(methylamino)-1,6-naphthyridin-2(1H)-one (1.6 g, 72% yield) 1H NMR (300 MHz, DMSO-d6): δ 8.36 (s, 1 H), 7.66 (s, 1 H), 7.17 (d, J=10.8 Hz, 1 H), 7.05 (m, 1H), 6.71 (d, J=9.6 Hz, 1 H), 6.15 (s, 1 H), 5.30 (s, 2 H), 3.47 (s, 3 H), 3.42 (s, 1 H), 2.84 (d, J=4.4 Hz, 3 H); MS (ESI) m/z: 333.1 [M+H]+

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. concentrationThe mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in 10% aq. of HCl (50 mL)
  5. washthe aqueous layer was washed with EtOAc
  6. extractionextracted with EtOAc (3×50 mL)
  7. washThe combined organics were washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3270adaabf0e4996896548c3cdf1ffbb
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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