Diisopropylethylamine → {6-Fluoro-4-[1-(pyridine-2-sulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester

HRID 2363829Notes

Reaction equation

HRID 2363829 reaction equation
C(N(C(C)C)CC)(C)C.FC(F)(F)C(O)=O.[CH3:17][O:18][C:19](=[O:38])[CH2:20][C:21]1[CH:30]=[C:29]([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([F:37])[CH:27]=2)[CH:22]=1.[N:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[S:45](Cl)(=[O:47])=[O:46]>C(Cl)Cl>[CH3:17][O:18][C:19](=[O:38])[CH2:20][C:21]1[CH:30]=[C:29]([CH:31]2[CH2:36][CH2:35][N:34]([S:45]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][N:39]=3)(=[O:47])=[O:46])[CH2:33][CH2:32]2)[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([F:37])[CH:27]=2)[CH:22]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3787675Pyridine-2-sulfonyl ChlorideHCID 86686887HCID 86686887, compound

Product 1

HCID 86686894{6-Fluoro-4-[1-(pyridine-2-sulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl esterYield 30.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diisopropylethylamine (0.4 mL, 2.3 mmol) was added at 0° C. to a solution of (6-fluoro-4-piperidin-4-yl-naphthalen-2-yl)-acetic acid methyl ester trifluoroacetate salt (which may be prepared as described above; 100 mg, 0.24 mmol) in CH2Cl2 (6 mL). The solution was stirred at room temperature for 30 min and then a solution of pyridine-2-sulfonyl chloride (which may be prepared as described above; 213 mg, 1.2 mmol) in CH2Cl2 (1 mL) was added. The mixture was stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure The residue was purified by chromatography on silica gel using a Biotage purification system, eluting with 25% ethyl acetate/hexanes, to give {6-fluoro-4-[1-(pyridine-2-sulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (32 mg, 30%) as a white solid. MS cald. for C23H24FN2O4S [(M+H)+]: 443, obsd. 443.3.

Workup

  1. stirringThe mixture was stirred at room temperature for 16 h
  2. customThe solvent was evaporated under reduced pressure The residue
  3. customwas purified by chromatography on silica gel using
  4. customa Biotage purification system
  5. washeluting with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-f90a9dc1addf4e028af6bc4e73e354f6
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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