Trifluoroacetic acid → HCID 86713618, compound

HRID 1257140Notes

Reaction equation

HRID 1257140 reaction equation
C(O)(C(F)(F)F)=O.COC1C=CC([CH2:14][N:15](C)[C:16]2[CH:25]=[C:24]3[C:19]([CH:20]=[C:21]([C:30]4[CH:35]=[C:34]([NH2:36])[C:33]([F:37])=[CH:32][C:31]=4[Cl:38])[C:22](=[O:29])[N:23]3[CH:26]([CH3:28])[CH3:27])=[CH:18][N:17]=2)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>O>[NH2:36][C:34]1[C:33]([F:37])=[CH:32][C:31]([Cl:38])=[C:30]([C:21]2[C:22](=[O:29])[N:23]([CH:26]([CH3:27])[CH3:28])[C:24]3[C:19]([CH:20]=2)=[CH:18][N:17]=[C:16]([NH:15][CH3:14])[CH:25]=3)[CH:35]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 86713619HCID 86713619, compound

Product 1

HCID 86713618HCID 86713618, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

TFA (5.55 g, 48.7 mmol) was added to 7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-2-chloro-4-fluorophenyl)-1-isopropyl-1,6-naphthyridin-2(1H)-one (0.78 g, 1.62 mmol) and the reaction was stirred for 90 min at RT. Water (50 mL) was added and the reaction mixture was carefully treated with solid Na2CO3 until it was faintly basic. The solution was extracted with EtOAc (2×), and the combined organics were washed with brine, dried (Na2SO4), concentrated in vacuo and purified by silica gel chromatography (MeOH/DCM) to afford 3-(5-amino-2-chloro-4-fluorophenyl)-1-isopropyl-7-(methylamino)-1,6-naphthyridin-2(1H)-one (0.42 g, 72% yield) as a white amorphous solid. 1H NMR (400 MHz, DMSO-d6): δ 8.34 (s, 1H), 7.60 (s, 1H), 7.17 (d, J=11.2 Hz, 1H), 6.95 (q, J=4.8 Hz, 1H), 6.71 (d, J=9.6 Hz, 1H), 6.41 (s, 1H), 5.30 (s, 2H), 5.08 (br s, 1H), 2.84 (d, J=4.8 Hz, 3H), 1.49 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 361.0 [M+H]+.

Workup

  1. extractionThe solution was extracted with EtOAc (2×)
  2. washthe combined organics were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-e51f4f80a89c484092ce0e96edc46230
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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