Trifluoroacetic acid → HCID 69296251, compound

HRID 1930318Notes

Reaction equation

HRID 1930318 reaction equation
FC(F)(F)C(O)=O.COC1C=CC([CH2:14][N:15](C)[C:16]2[CH:25]=[C:24]3[C:19]([CH:20]=[C:21]([C:28]4[CH:33]=[C:32]([NH2:34])[CH:31]=[CH:30][C:29]=4[Cl:35])[C:22](=[O:27])[N:23]3[CH3:26])=[CH:18][N:17]=2)=CC=1>C(Cl)Cl>[NH2:34][C:32]1[CH:31]=[CH:30][C:29]([Cl:35])=[C:28]([C:21]2[C:22](=[O:27])[N:23]([CH3:26])[C:24]3[C:19]([CH:20]=2)=[CH:18][N:17]=[C:16]([NH:15][CH3:14])[CH:25]=3)[CH:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69298125HCID 69298125, compound

Product 1

HCID 69296251HCID 69296251, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (10 mL, 134 mmol) was added to a solution of 7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-2-chlorophenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (4 g, 9.2 mmol) in CH2Cl2 (50 mL). The mixture was heated to reflux for 3 hrs. The reaction mixture was concentrated under reduced pressure, dissolved in aq HCl solution and washed with EtOAc (3×50 mL). The aqueous layer was neutralized with saturated Na2CO3 solution to pH 8, and was extracted with EtOAc (3×50 mL). The combined extracts were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by chromatography to give 3-(5-amino-2-chlorophenyl)-1-methyl-7-(methylamino)-1,6-naphthyridin-2(1H)-one (1.7 g, 58% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.36 (s, 1 H), 7.63 (s, 1 H), 7.06-7.00 (m, 2 H), 6.54-6.50 (m, 2 H), 6.14 (s, 1 H), 5.21 (s, 2 H), 3.48 (s, 3 H), 2.84 (d, J=4.8 Hz, 3 H); MS (ESI) m/z: 314.9 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hrs
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutiondissolved in aq HCl solution
  5. washwashed with EtOAc (3×50 mL)
  6. extractionwas extracted with EtOAc (3×50 mL)
  7. washThe combined extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-ece1f62921d743d599af399a9d2bc0ff
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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