Diisopropylethylamine → HCID 86686911, compound

HRID 2363864Notes

Reaction equation

HRID 2363864 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.[CH3:40][O:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=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:43]3[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=3[O:41][CH3:40])(=[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 37458512-Methoxybenzenesulfonyl ChlorideHCID 86686889HCID 86686889, compound

Product 1

HCID 86686911HCID 86686911, compoundYield 55.6%

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-methoxybenzenesulfonyl chloride (98 mg, 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 4 hours at room temperature under nitrogen. During this time, some solvent had evaporated. Additional methylene chloride was added. The reaction mixture was diluted with water (˜25 mL) and extracted with methylene chloride (3×25 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated. Silica gel chromatography (20-33% ethyl acetate/hexanes) afforded {6-fluoro-4-[1-(2-methoxy-benzenesulfonyl)-piperidin-4-yl]-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (64 mg, 55%). MS cald. for C26H29FNO5S [(M+H)+]: 486, obsd. 486.2.

Workup

  1. temperatureto warm to room temperature
  2. stirringwas stirred for 4 hours at room temperature under nitrogen
  3. customDuring this time, some solvent had evaporated
  4. additionAdditional methylene chloride was added
  5. additionThe reaction mixture was diluted with water (˜25 mL)
  6. extractionextracted with methylene chloride (3×25 mL)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over anhydrous MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-2f58086a3c0042dcbac9eedd253a2728
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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