2,5-Dichlorobenzenesulfonyl chloride → HCID 86686908, compound

HRID 2363858Notes

Reaction equation

HRID 2363858 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]([Cl:47])=[CH:43][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[CH:43]=[C:44]([Cl:47])[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 794012,5-Dichlorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86686889HCID 86686889, compound

Product 1

HCID 86686908HCID 86686908, compoundYield 42%

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 2,5-dichlorobenzenesulfonyl chloride (116 mg, 0.474 mmol). After stirring for ˜15 minutes at 0° C., the light yellow reaction mixture was allowed to warm to room temperature and then was stirred overnight at room temperature under nitrogen. During this time, some solvent evaporated. Methylene chloride (˜10 mL) and water (˜25 mL) were added. The resulting mixture was extracted with methylene chloride (2×25 mL). The combined extracts were washed with brine solution then concentrated to give the crude product which was purified by elution from a silica gel plug (20% ethyl acetate in hexanes) to give {4-[1-(2,5-dichloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (52 mg, 42%) as an off-white solid. MS cald. for C25H25Cl2FNO4S [(M+H)+]: 524, obsd. 524.0.

Workup

  1. temperatureto warm to room temperature
  2. stirringwas stirred overnight at room temperature under nitrogen
  3. customDuring this time, some solvent evaporated
  4. additionMethylene chloride (˜10 mL) and water (˜25 mL) were added
  5. extractionThe resulting mixture was extracted with methylene chloride (2×25 mL)
  6. washThe combined extracts were washed with brine solution
  7. concentrationthen concentrated
  8. customto give the crude product which
  9. customwas purified by elution from a silica gel plug (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0bda30b3ad6b40d599fcc37226a40a25
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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