Benzene, 1-isocyanato-2-methoxy- → HCID 86686926, compound

HRID 2363891Notes

Reaction equation

HRID 2363891 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.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]=[C:33]=[O:34]>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:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[O:25][CH3:24])[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 69695Benzene, 1-isocyanato-2-methoxy-HCID 86686890HCID 86686890, compound

Product 1

HCID 86686926HCID 86686926, compoundYield 87.4%

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; 83.6 mg, 0.265 mmol) in methylene chloride (8.0 mL) was added 2-methoxyphenyl isocyanate (71 μL, 0.53 mmol) at room temperature under nitrogen. The resulting light brown solution was stirred at room temperature for 10 minutes. The reaction mixture was diluted with water (˜25 mL) and the resulting mixture was extracted with methylene chloride (2×30 mL). The combined organic layers were washed with saturated aqueous NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated to a light yellow film. Flash chromatography (0-60% ethyl acetate in hexanes) provided {6-fluoro-4-[1-(2-methoxy-phenylcarbamoyl)-piperidin-4-yl]-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (107.6 mg, 87%) as a colorless film. MS cald. for C27H30FN2O4 [(M+H)+]: 465, obsd. 465.3.

Workup

  1. extractionthe resulting mixture was extracted with methylene chloride (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 light yellow film

Sources & evidence

ORD record
ord-7ebc4ee0b0b64c9997210f4c81ea3426
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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