Diisopropylethylamine → HCID 86686909, compound

HRID 2363860Notes

Reaction equation

HRID 2363860 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][CH:44]=[C:43]([Cl:47])[C:42]=1[S:48](Cl)(=[O:50])=[O:49]>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:42]3[C:43]([Cl:47])=[CH:44][CH:45]=[CH:46][C:41]=3[Cl:40])(=[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

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5221832,6-DichlorobenzenesulfonylchlorideHCID 86686889HCID 86686889, compound

Product 1

HCID 86686909HCID 86686909, compoundYield 77.2%

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 2,6-dichlorobenzenesulfonyl chloride (116 mg, 0.47 mmol). After stirring for ˜25 minutes at 0° C., the light yellow reaction mixture was allowed to warm to room temperature and then was stirred for 6.5 hours at room temperature under nitrogen. During this time, some solvent had evaporated. Methylene chloride (˜10 mL) and water (˜25 mL) were added and the mixture was extracted with methylene chloride (2×25 mL). The combined extracts were washed with brine solution, dried over anhydrous MgSO4, filtered, concentrated, and purified by silica gel chromatography (eluting with 25% ethyl acetate/hexanes) to give {4-[1-(2,6-dichloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (96 mg, 77%) as a light yellow product. MS cald. for C25H25Cl2FNO4S [(M+H)+]: 524, obsd. 524.1.

Workup

  1. temperatureto warm to room temperature
  2. stirringwas stirred for 6.5 hours at room temperature under nitrogen
  3. customDuring this time, some solvent had evaporated
  4. additionMethylene chloride (˜10 mL) and water (˜25 mL) were added
  5. extractionthe mixture was extracted with methylene chloride (2×25 mL)
  6. washThe combined extracts were washed with brine solution
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by silica gel chromatography (eluting with 25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-aedd84731e9b45cba9743c212b1e8f43
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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