3-(Trifluoromethyl)phenyl isocyanate → HCID 86686927, compound

HRID 2363893Notes

Reaction equation

HRID 2363893 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:22])[CH:11]=2)[CH:6]=1.[F:24][C:25]([F:36])([F:35])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([N:32]=[C:33]=[O:34])[CH:27]=1>C(Cl)Cl.O>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([CH:16]2[CH2:17][CH2:18][N:19]([C:33](=[O:34])[NH:32][C:28]3[CH:29]=[CH:30][CH:31]=[C:26]([C:25]([F:24])([F:36])[F:35])[CH:27]=3)[CH2:20][CH2:21]2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:22])[CH:11]=2)[CH:6]=1

Participants

5

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 86686890HCID 86686890, compound

Product 1

HCID 86686927HCID 86686927, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-fluoro-3-methyl-4-piperidin-4-yl-naphthalen-2-yl)-acetic acid methyl ester (which may be prepared as described above; 94 mg, 0.298 mmol) in methylene chloride (6.0 mL) was added trifluoro-m-tolyl isocyanate (82 μL, 0.596 mmol) at room temperature under nitrogen. The resulting light brown solution was stirred at room temperature for 40 minutes. The reaction mixture was diluted with water (˜25 mL) and the resulting mixture was extracted with methylene chloride (3×25 mL). The combined organic layers were washed with saturated aqueous NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated to a yellow-orange film. Silica gel chromatography (20-25% ethyl acetate in hexanes) provided {6-fluoro-3-methyl-4-[1-(3-trifluoromethyl-phenylcarbamoyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (97 mg, 65%) as a colorless film. MS cald. for C27H27F4N2O3 [(M+H)+]: 503, obsd. 503.2.

Workup

  1. extractionthe resulting mixture was extracted with methylene chloride (3×25 mL)
  2. washThe combined organic layers were washed with saturated aqueous NaHCO3
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to a yellow-orange film

Sources & evidence

ORD record
ord-fc935b513047415ebcc11ca1b58ccba9
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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