Diisopropylethylamine → HCID 86686913, compound

HRID 2363866Notes

Reaction equation

HRID 2363866 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:30])[CH2:11][C:12]1[C:21]([CH3:22])=[C:20]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([F:29])[CH:18]=2)[CH:13]=1.C(N(CC)C(C)C)(C)C.[Cl:40][C:41]1[CH:42]=[C:43]([CH2:47][S:48](Cl)(=[O:50])=[O:49])[CH:44]=[CH:45][CH:46]=1>C(Cl)Cl.O>[CH3:8][O:9][C:10](=[O:30])[CH2:11][C:12]1[C:21]([CH3:22])=[C:20]([CH:23]2[CH2:24][CH2:25][N:26]([S:48]([CH2:47][C:43]3[CH:44]=[CH:45][CH:46]=[C:41]([Cl:40])[CH:42]=3)(=[O:49])=[O:50])[CH2:27][CH2:28]2)[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([F:29])[CH:18]=2)[CH:13]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2757802(3-Chlorophenyl)methanesulfonyl chlorideHCID 86686889HCID 86686889, compound

Product 1

HCID 86686913HCID 86686913, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of (6-fluoro-3-methyl-4-piperidin-4-yl-naphthalen-2-yl)-acetic acid methyl ester trifluoroacetate salt (which may be prepared as described above; 102 mg, 0.237 mmol) and N,N-diisopropylethylamine (124 μL, 0.711 mmol) in methylene chloride (6.0 mL) was added (3-chloro-phenyl)-methanesulfonyl chloride (106.7 mg, 0.474 mmol). The reaction mixture was stirred at 0° C. for 10 minutes, then it was warmed to room temperature and stirred at room temperature overnight. The reaction mixture was diluted with water. The resulting mixture was extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered, and concentrated. Silica gel chromatography (20-25% ethyl acetate in hexanes) provided {4-[1-(3-chloro-phenylmethanesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (52.4 mg, 44%) as a colorless film. MS cald. For C26H28ClFNO4S [(M+H)+]: 504, obsd. 504.1.

Workup

  1. temperatureit was warmed to room temperature
  2. stirringstirred at room temperature overnight
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0af6ee79bc7145658271cf24a35f85cf
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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