Diisopropylethylamine → HCID 86686896, compound

HRID 2363834Notes

Reaction equation

HRID 2363834 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][C:42]([S:45](Cl)(=[O:47])=[O:46])=[CH:41][CH:40]=1>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:42]3[CH:43]=[CH:44][N:39]=[CH:40][CH:41]=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 11586382Pyridine-4-sulfonyl ChlorideHCID 86686887HCID 86686887, compound

Product 1

HCID 86686896HCID 86686896, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diisopropylethylamine (0.3 mL, 1.7 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-4-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 to give {6-fluoro-4-[1-(pyridine-4-sulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (45 mg, 42%) as an orange liquid. MS cald. for C23H24FN2O4S [(M+H)+]: 443, obsd. 443.4.

Workup

  1. stirringThe mixture was stirred at room temperature for 16 h
  2. customThe solvent was evaporated under reduced pressure
  3. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-1b442b2a60c34b54a9d345d4c8f8a8ed
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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