Trifluoroacetic acid → HCID 69296327, compound

HRID 1930315Notes

Reaction equation

HRID 1930315 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10](=[O:33])[N:11]([CH:30]([CH3:32])[CH3:31])[C:12]3[C:17]([CH:18]=2)=[CH:16][N:15]=[C:14]([N:19](CC2C=CC(OC)=CC=2)[CH3:20])[CH:13]=3)[CH:5]=[CH:6][C:7]=1[F:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10](=[O:33])[N:11]([CH:30]([CH3:31])[CH3:32])[C:12]3[C:17]([CH:18]=2)=[CH:16][N:15]=[C:14]([NH:19][CH3:20])[CH:13]=3)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69037725HCID 69037725, compound

Product 1

HCID 69296327HCID 69296327, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above prepared 3-(3-amino-4-fluoro-phenyl)-1-isopropyl-7-[(4-methoxy-benzyl)-methyl-amino]-1H-[1,6]naphthyridin-2-one (5.3 g) was combined in DCM (150 mL) with TFA (50 mL) and the resultant mixture was heated at reflux overnight. The volatiles were removed under reduced pressure, and the residue was dissolved in 10% HCl aqueous solution. The aqueous layer was washed with EtOAc (3×100 mL) and the aqueous layer was basified to pH 11, and extracted with EtOAc. The combined extracts were dried (Na2SO4) and concentrated to give 3-(3-amino-4-fluoro-phenyl)-1-isopropyl-7-methylamino-1H-[1,6]naphthyridin-2-one (1.26 g, 32% yield for two steps). 1H NMR (400 MHz, DMSO-d6): δ 8.36 (s, 1 H), 7.70 (s, 1 H), 7.06 (dd, J=8.4, 2.0 Hz, 1 H), 6.94 (dd, J=11.6, 8.4 Hz, 1 H), 6.88 (m, 1 H), 6.72 (m, 1 H), 6.39 (s, 1 H), 5.07 (m, 1 H), 5.06 (s, 2 H), 2.83 (d, J=4.8 Hz, 1 H), 1.51 (d, J=6.8 Hz, 6 H); MS (ESI) m/z: 327.1 [M+H]+.

Workup

  1. temperatureat reflux overnight
  2. customThe volatiles were removed under reduced pressure
  3. dissolutionthe residue was dissolved in 10% HCl aqueous solution
  4. washThe aqueous layer was washed with EtOAc (3×100 mL)
  5. extractionextracted with EtOAc
  6. dry with materialThe combined extracts were dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-84fc9082d2964f708d2f56f2a6418a77
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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