2,4-Dichlorophenyl isocyanate → HCID 86686924, compound

HRID 2363887Notes

Reaction equation

HRID 2363887 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.[Cl:24][C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=1[N:32]=[C:33]=[O:34]>CO.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:26]3[CH:27]=[CH:28][C:29]([Cl:31])=[CH:30][C:25]=3[Cl:24])[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 757892,4-Dichlorophenyl isocyanateHCID 86686890HCID 86686890, compound

Product 1

HCID 86686924HCID 86686924, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

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; 47.2 mg, 0.150 mmol) in methanol (6.0 mL) was added neat 2,4-dichlorophenyl isocyanate (56.4 mg, 0.300 mmol) at room temperature under nitrogen. The resulting light brown solution was stirred at room temperature for 15 minutes. The reaction mixture was diluted with water (˜25 mL) and the resulting mixture was extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with saturated aqueous NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated to a colorless film. Silica gel chromatography (20-25% ethyl acetate in hexanes) provided {4-[1-(2,4-dichloro-phenylcarbamoyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (74.8 mg, 99%) as a colorless film. MS cald. for C26H26Cl2FN2O3 [(M+H)+]: 503, obsd. 503.1.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (2×30 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 colorless film

Sources & evidence

ORD record
ord-f499c5c48228449db6c662a701b52a51
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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