Diisopropylethylamine → HCID 86686914, compound

HRID 2363868Notes

Reaction equation

HRID 2363868 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:46]=[CH:45][C:44]([CH2:47][S:48](Cl)(=[O:50])=[O:49])=[CH:43][CH:42]=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:44]3[CH:45]=[CH:46][C:41]([Cl:40])=[CH:42][CH:43]=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 227304(4-Chlorophenyl)methanesulfonyl chlorideHCID 86686889HCID 86686889, compound

Product 1

HCID 86686914HCID 86686914, compoundYield 24%

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 (4-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 for four hours. The reaction mixture was diluted with water (25 mL). The resulting mixture was extracted with ethyl acetate (2×25 mL). The organic phase was dried over MgSO4, filtered, and concentrated. Silica gel chromatography (20-25% ethyl acetate in hexanes) provided {4-[1-(4-chloro-phenylmethanesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (28.5 mg, 24%) as a colorless film. MS cald. For C26H28ClFNO4S [(M+H)+]: 504, obsd. 504.2.

Workup

  1. temperatureit was warmed to room temperature
  2. stirringstirred at room temperature for four hours
  3. extractionThe resulting mixture was extracted with ethyl acetate (2×25 mL)
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-13e1c41c142b408a85742377b9ea354c
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

Loading…