Trifluoroacetic acid → HCID 69296327, compound

HRID 1430438Notes

Reaction equation

HRID 1430438 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 with TFA (50 mL) in DCM (150 mL) and heated at reflux overnight. The volatiles were removed under reduced pressure, the residue dissolved in 10% HCl and washed with EtOAc (3×). The aqueous layer was made basic (pH=11), extracted with EtOAc and the combined organics 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 over two steps). 1H NMR (400 MHz, DMSO-d6): δ 8.36 (s, 1H), 7.70 (s, 1H), 7.06 (dd, J=8.4, 2.0 Hz, 1H), 6.94 (dd, J=11.6, 8.4 Hz, 1H), 6.88 (m, 1H), 6.72 (m, 1H), 6.39 (s, 1H), 5.07 (m, 1H), 5.06 (s, 2H), 2.83 (d, J=4.8 Hz, 1H), 1.51 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 327.1 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customThe volatiles were removed under reduced pressure
  4. dissolutionthe residue dissolved in 10% HCl
  5. washwashed with EtOAc (3×)
  6. extractionextracted with EtOAc
  7. dry with materialthe combined organics were dried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3e39ba0030b54a9ab44ed0e266d226d0
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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