Trifluoroacetic acid → HCID 69299467, compound

HRID 1930291Notes

Reaction equation

HRID 1930291 reaction equation
COC1C=CC([CH2:7][N:8](C)[C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([C:21]4[CH:26]=[C:25]([NH2:27])[C:24]([F:28])=[CH:23][C:22]=4[CH3:29])[C:15](=[O:20])[N:16]3[CH3:19])=[CH:11][N:10]=2)=CC=1.C(C(O)=O)(F)(F)F.C([O-])([O-])=O.[Na+].[Na+]>>[NH2:27][C:25]1[C:24]([F:28])=[CH:23][C:22]([CH3:29])=[C:21]([C:14]2[C:15](=[O:20])[N:16]([CH3:19])[C:17]3[C:12]([CH:13]=2)=[CH:11][N:10]=[C:9]([NH:8][CH3:7])[CH:18]=3)[CH:26]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 69297936HCID 69297936, compound

Product 1

HCID 69299467HCID 69299467, compoundYield 64%

Procedure

7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-4-fluoro-2-methylphenyl)-1-methyl-1, 6-naphthyridin-2(1H)-one (1.86 g, 4.3 mmol, 1.0 eq) and CF3CO2H (9.5 ml, 13.8 g, 121 mmol, 28 eq) were combined and stirred at RT overnight. The completed reaction was treated slowly with 2M Na2CO3 until the mixture was just faintly basic. The resulting suspension was stirred at RT for 1 h. The solids were collected by filtration, washed thoroughly with H2O, dried partially in the air and then under high vacuum at 65° C. The crude product was purified by flash column chromatography (100% EtOAc to 25% THF/EtOAc) to afford 3-(5-amino-4-fluoro-2-methylphenyl)-1-methyl-7-(methylamino)-1,6-naphthyridin-2(1H)-one (0.86 g, 64% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.35 (s, 1H), 7.58 (s, 1H), 6.99 (q, J=4.8 Hz, 1H), 6.56 (d, J=12.0 Hz, 1H), 6.56 (d, J=9.2 Hz, 1H), 6.15 (s, 1H), 4.87 (brs, 2H), 3.48 (s, 3H), 2.84 (d, J=5.2 Hz, 3H), 1.94 (s, 3H); MS (ESI) m/z: 313.2 (M+H+).

Workup

  1. customThe completed reaction
  2. stirringThe resulting suspension was stirred at RT for 1 h
  3. filtrationThe solids were collected by filtration
  4. washwashed thoroughly with H2O
  5. customdried partially in the air
  6. customat 65° C
  7. customThe crude product was purified by flash column chromatography (100% EtOAc to 25% THF/EtOAc)

Sources & evidence

ORD record
ord-922a661476924125b4bbab40457208be
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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