4-(Trifluoromethyl)aniline → HCID 59811134, compound

HRID 2113627Notes

Reaction equation

HRID 2113627 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([CH2:26][O:27][CH3:28])=[N:7][C:8]2[C:13]([C:14]=1Cl)=[CH:12][CH:11]=[C:10]([C:16]1[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:19]=[CH:18][N:17]=1)[N:9]=2)=[O:4].[F:29][C:30]([F:39])([F:38])[C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[C:6]([CH2:26][O:27][CH3:28])=[N:7][C:8]2[C:13]([C:14]=1[NH:35][C:34]1[CH:36]=[CH:37][C:31]([C:30]([F:29])([F:38])[F:39])=[CH:32][CH:33]=1)=[CH:12][CH:11]=[C:10]([C:16]1[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:19]=[CH:18][N:17]=1)[N:9]=2)=[O:4]

Participants

4

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 59811133HCID 59811133, compound

Product 1

HCID 59811134HCID 59811134, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dissolve 4-chloro-2-methoxymethyl-7-(3-trifluoromethyl-pyridin-2-yl)-[1,8]napthyridine-3-carboxylic acid methyl ester (0.57 g, 1.4 mmol) and 4-trifluoromethyl aniline (234 mg, 1.53 mmol) in acetonitrile (10 mL). Stir overnight at room temperature. Remove the solvent under reduced pressure and dissolve the crude product in EtOAc (25 mL) and saturated NaHCO3 (aq) (25 mL). Remove the organic layer and dry over Na2SO4. Remove the solvent under reduced pressure and chromatograph the crude mixture on silica gel eluting with hexane/acetone (2:1) to yield the title compound. MS 537.18 (M+1).

Workup

  1. customRemove the solvent under reduced pressure
  2. dissolutiondissolve the crude product in EtOAc (25 mL) and saturated NaHCO3 (aq) (25 mL)
  3. customRemove the organic layer
  4. dry with materialdry over Na2SO4
  5. customRemove the solvent under reduced pressure and chromatograph the crude mixture on silica gel eluting with hexane/acetone (2:1)

Sources & evidence

ORD record
ord-33a2d00f64b74bb9a93d08adf582cc68
Source dataset
uspto-grants-2008_10
Patent number
US07432275B2

Reaction notes

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