Trifluoroacetic acid → HCID 86713620, compound

HRID 1430432Notes

Reaction equation

HRID 1430432 reaction equation
COC1C=CC([CH2:7][N:8](C)[C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([C:23]4[CH:28]=[C:27]([NH2:29])[C:26]([F:30])=[CH:25][C:24]=4[CH3:31])[C:15](=[O:22])[N:16]3[CH:19]([CH3:21])[CH3:20])=[CH:11][N:10]=2)=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:29][C:27]1[C:26]([F:30])=[CH:25][C:24]([CH3:31])=[C:23]([C:14]2[C:15](=[O:22])[N:16]([CH:19]([CH3:20])[CH3:21])[C:17]3[C:12]([CH:13]=2)=[CH:11][N:10]=[C:9]([NH:8][CH3:7])[CH:18]=3)[CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86713621HCID 86713621, compound

Product 1

HCID 86713620HCID 86713620, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-4-fluoro-2-methylphenyl)-1-isopropyl-1,6-naphthyridin-2(1H)-one (1.0 g, 2.2 mmol) in DCM (10 mL) was added TFA (3 mL) at RT. The resulting mixture was stirred at RT for 6 h, then washed with H2O (6×). The combined aqueous layers were neutralized with NH3H2O, extracted with DCM (3×) and the combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated to give 3-(5-amino-4-fluoro-2-methylphenyl)-1-isopropyl-7-(methylamino)-1,6-naphthyridin-2(1H)-one (0.5 g, 66.8% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.41 (s, 1H), 7.60 (s, 1H), 6.95 (m, 1H), 6.90 (d, J=12.4 Hz, 1H), 6.65 (d, J=9.2 Hz, 1H), 6.50 (s, 1H), 5.21 (br s, 1H), 4.95 (s, 2H), 2.92 (d, J=4.8 Hz, 3H), 2.02 (s, 3H), 1.58 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 341.2[M+H]+.

Workup

  1. washwashed with H2O (6×)
  2. extractionextracted with DCM (3×)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8247682d79ac427c812fd19326ccd3fa
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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