3-(Trifluoromethyl)aniline → HCID 86608616, compound

HRID 1925298Notes

Reaction equation

HRID 1925298 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15]([C:19](Cl)=[O:20])=[CH:14][CH:13]=[CH:12]3)[CH:5]=[CH:4][N:3]=1.[F:22][C:23]([F:32])([F:31])[C:24]1[CH:25]=[C:26]([NH2:30])[CH:27]=[CH:28][CH:29]=1>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15]([C:19]([NH:30][C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([C:23]([F:22])([F:31])[F:32])[CH:25]=2)=[O:20])=[CH:14][CH:13]=[CH:12]3)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 866086176-(2-Chloropyrimidin-4-yloxy)-1-naphthoyl chloride

Product 1

HCID 86608616HCID 86608616, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of the hydrochloride salt of 6-(2-chloropyrimidin-4-yloxy)-1-naphthoyl chloride (step b, 0.122 g, 0.34 mmol) in THF (3 mL) was added 3-(trifluoromethyl)benzenamine (0.047 mL, 0.38 mmol). The reaction was stirred at RT overnight. The mixture was concentrated and partitioned between EtOAc and 2N aqueous NaOH. Extraction with several portions of EtOAc was followed by washing of the organic layer with brine and drying with MgSO4. The solution was filtered and concentrated to afford the desired compound.

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between EtOAc and 2N aqueous NaOH
  3. extractionExtraction with several portions of EtOAc
  4. washby washing of the organic layer with brine
  5. dry with materialdrying with MgSO4
  6. filtrationThe solution was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a0d76452876e4bfb8f5e363f1d7b71eb
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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