Water → HCID 86686915, compound

HRID 2363870Notes

Reaction equation

HRID 2363870 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.[F:40][C:41]([F:53])([F:52])[C:42]1[CH:43]=[C:44]([S:48](Cl)(=[O:50])=[O:49])[CH:45]=[CH:46][CH:47]=1.O>C(Cl)Cl>[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]([C:44]3[CH:45]=[CH:46][CH:47]=[C:42]([C:41]([F:40])([F:52])[F:53])[CH:43]=3)(=[O:50])=[O:49])[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 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 86686889HCID 86686889, compound

Product 1

HCID 86686915HCID 86686915, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 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-(trifluoromethyl)benzenesulfonyl chloride (76 μL, 0.474 mmol). After stirring for ˜10 minutes at 0° C., the light yellow reaction mixture was allowed to warm to room temperature and then was stirred for overnight at room temperature. Water (˜25 mL) was added and the mixture was extracted with methylene chloride (2×30 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated. Silica gel chromatography (25-33% ethyl acetate in hexanes) afforded {6-fluoro-3-methyl-4-[1-(3-trifluoromethyl-benzenesulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (104 mg, 84%). MS cald. for C26H26F4NO4S [(M+H)+]: 524, obsd. 524.1.

Workup

  1. temperatureto warm to room temperature
  2. stirringwas stirred for overnight at room temperature
  3. extractionthe mixture was extracted with methylene chloride (2×30 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3af30a49255a4d31983a688b355cf888
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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