Trifluoroacetic acid → HCID 69041164, compound

HRID 1930301Notes

Reaction equation

HRID 1930301 reaction equation
COC1C=CC([CH2:7][N:8](C)[C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[C:28]([NH2:33])[CH:27]=4)[C:15](=[O:25])[N:16]3[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:11][N:10]=2)=CC=1.C(C(O)=O)(F)(F)F>C(Cl)Cl>[NH2:33][C:28]1[CH:27]=[C:26]([C:14]2[C:15](=[O:25])[N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:17]3[C:12]([CH:13]=2)=[CH:11][N:10]=[C:9]([NH:8][CH3:7])[CH:18]=3)[CH:31]=[CH:30][C:29]=1[F:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69298864HCID 69298864, compound

Product 1

HCID 69041164HCID 69041164, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of Example A35 (2.5 g, 7 mmol) in 4-methoxybenzylmethylamine (5 mL) was heated at 160° C. for 3 h. The reaction mixture was cooled to RT and diluted with ether. The resultant white precipitate was collected by filtration and dried to obtained 7-((4-methoxybenzyl)(methyl)amino)3-(3-amino-4-fluorophenyl)-1-phenyl-1,6-naphthyridin-2(1H)-one (3 g, 77%), which was used in the next step without further purification. A suspension of 7-((4-methoxybenzyl)(methyl)amino)-3-(3-amino-4-fluorophenyl)-1-phenyl-1,6-naphthyridin-2(1H)-one (3.0 g, 6 mmol) in mixture of CF3CO2H and CH2Cl2 (3:7, 30 mL) was heated at reflux overnight. Then the solvent was removed under reduced pressure and the residue was recrystallized (EtOAc-petroleum ether) to give 3-(3-amino-4-fluorophenyl)-7-(methylamino)-1-phenyl-1,6-naphthyridin-2(1H)-one (1 g, 45% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.43 (s, 1 H), 7.88 (s, 1 h), 7.60-7.50 (m, 3 H), 7.31-7.29 (m, 2 H), 7.10-6.75 (m, 4H), 5.26 (s, 1 H), 5.08 (s, 2 H), 2.63 (br s, 3 H); MS (ESI) m/z: 361.3 [M+H]+.

Workup

  1. customwas used in the next step without further purification
  2. temperaturewas heated
  3. temperatureat reflux overnight
  4. customThen the solvent was removed under reduced pressure
  5. customthe residue was recrystallized (EtOAc-petroleum ether)

Sources & evidence

ORD record
ord-894a9c8b1c074b84a5e16b3c737825b1
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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